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Recent Developments and Applications in Enantioselective Desymmetrisation. Xin Linghu Department of Chemistry University of North Carolina, Chapel Hill. Outline. Introduction Enantioselective Desymmetrisation of Different Functional Groups Cyclic anhydrides Epoxides

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Recent developments and applications in enantioselective desymmetrisation

Recent Developments and Applications in Enantioselective Desymmetrisation

Xin Linghu

Department of Chemistry

University of North Carolina, Chapel Hill


Outline

Outline

  • Introduction

  • Enantioselective Desymmetrisation

    of Different Functional Groups

  • Cyclic anhydrides

  • Epoxides

  • Aldehydes and Ketones

  • Alkenes

  • Diols

  • Summary

  • Acknowledgement


Introduction to enantioselective desymmetrisation

Introduction to Enantioselective Desymmetrisation


Enantioselective desymmetrisation in total synthesis

Enantioselective Desymmetrisation in Total Synthesis

1987, Schreiber:

1992, Harada:


Enantioselective desymmetrisation of cyclic anhydride previous work

Enantioselective Desymmetrisation of Cyclic Anhydride: Previous Work

1985, Oda:

configuration

1999, Bolm:

1995, Seebach:


Formation of c x bond via anhydrides

Formation of C-X Bond via Anhydrides

Chen, Y.; Tian, S.-K.; Deng, L. J. Am. Chem. Soc. 2000, 122, 9542-9543.


Formation of c c bond via anhydrides

Formation of C-C Bond via Anhydrides

Bercot, E. A.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 174-175.


Formation of c c bond via anhydrides1

Formation of C-C Bond via Anhydrides

Shintani, R.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 1057-1059.


Formation of c c bond via anhydrides2

Formation of C-C Bond via Anhydrides

Shintani, R.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 1057-1059.


Enantioselective desymmetrisation of epoxides previous work

Enantioselective Desymmetrisation of Epoxides: Previous Work


Enantioselective desymmetrisation of epoxides previous work1

Enantioselective Desymmetrisation of Epoxides: Previous Work

Cat. (10 mol), 4A MS


Enantioselective ring opening catalyzed by planar chiral pyridine n oxides

Enantioselective Ring Opening Catalyzed by Planar-Chiral Pyridine N-Oxides

Tao, B.; Lo, M. M. C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 353-354.


Enantioselective ring opening catalyzed by chiral bipyridine n n dioxide derivatives

Enantioselective Ring Opening Catalyzed by Chiral Bipyridine N,N’-Dioxide Derivatives

Nakajima, M.; Saito, M.; Uemura, M.; Hashimoto, S. Tetrahedron Lett.2002, 43, 8827-8829.


Asymmetric ring opening with tmscn catalyzed by pybox yb complexes

Asymmetric Ring Opening with TMSCN Catalyzed by (pybox)Yb Complexes

Schaus, S. E.; Jacobsen, E. N. Org. Lett.2000, 2, 1001-1004.


Enantioselective alkylation of vinyloxiranes

Enantioselective Alkylation of Vinyloxiranes

Bertozzi, F.; Crotti, P.; Macchia, F.; Pineschi, M.; Arnold, A.; Feringa, B. L. Org. Lett.2000, 2, 933-936.


Desymmetrisation by enantioselective deprotonation

Desymmetrisation by Enantioselective Deprotonation

Hodgson, D. M.; Gibbs, A. R.; Lee, G. P. Tetrahedron1996, 52, 14361-14384.


Enantioselective a deprotonation of epoxides previous work

Enantioselective a-Deprotonation of Epoxides: Previous Work

1996, Hodgson:

1996, Hodgson:


Enantioselective b deprotonation of epoxides previous work

Enantioselective b-Deprotonation of Epoxides: Previous Work

1980, Whitesell and

Felman:

1993, Milne and

Murphy:

1998, Andersson:


Enantioselective alkylative double ring opening of epoxides

Enantioselective Alkylative Double Ring Opening of Epoxides

Hodgson, D. M.; Maxwell, C. R.; Miles, T. J.; Paruch, E.; Stent, M. A. H.; Matthews, I. R.;

Wilson, F. X.; Witherington, J. Angew. Chem. Int. Ed. 2002, 41, 4313-4316.


Enantioselective alkylative double ring opening of epoxides1

Enantioselective Alkylative Double Ring Opening of Epoxides

Hodgson, D. M.; Maxwell, C. R.; Miles, T. J.; Paruch, E.; Stent, M. A. H.; Matthews, I. R.;

Wilson, F. X.; Witherington, J. Angew. Chem. Int. Ed. 2002, 41, 4313-4316.


A deprotonated epoxides as nucleophiles

a-Deprotonated Epoxides as Nucleophiles

Hodgson, D. M.; Gras, E. Angew. Chem. Int. Ed. 2002, 41, 2376-2378.


First desymmetrisation of centrosymmetric diepoxide in natural product synthesis

First Desymmetrisation of Centrosymmetric Diepoxide in Natural Product Synthesis

Holland, J. M.; Lewis, M.; Nelson, A. Angew. Chem. Int. Ed. 2001, 40, 4082-4084.


First desymmetrisation of centrosymmetric diepoxide in natural product synthesis1

First Desymmetrisation of Centrosymmetric Diepoxide in Natural Product Synthesis

Holland, J. M.; Lewis, M.; Nelson, A. Angew. Chem. Int. Ed. 2001, 40, 4082-4084.


Enantioselective desymmetrisation of ketones and aldehydes previous work

Enantioselective Desymmetrisation of Ketones and Aldehydes: Previous Work

1984, Hanessian:

1998, Arai and

Shioiri:

1990, Roush:

1998, Takemoto:


Enantioselective desymmetrisation of ketones and aldehydes previous work1

Enantioselective Desymmetrisation of Ketones and Aldehydes: Previous Work

1998, Ward:

1995, Aubé:

1997, Bolm:


Enantioselective baeyer villiger oxidations by transition metal catalysis

Enantioselective Baeyer-Villiger Oxidations by Transition Metal Catalysis

Uchida, T.; Katsuki, T.; Ito, K.; Akashi, S.; Ishii, A.; Kuroda, T. Helv. Chim. Acta 2002, 85, 3078-3089.

Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481-4485.


Enantioselective baeyer villiger oxidations by organocatalysis

Enantioselective Baeyer-Villiger Oxidations by Organocatalysis

Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem. Int. Ed. 2002, 41, 2366-2368.


Rhodium catalyzed desymmetrisation of 4 alkynals

Rhodium-Catalyzed Desymmetrisation of 4-Alkynals

Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2002, 124, 10296-10297.


Enantioselective reduction of 2 alkyl 1 3 diketones

Enantioselective Reduction of 2-Alkyl-1,3-diketones

Ohtsuka, Y.; Koyasu, K.; Ikeno, T.; Yamada, T. Org. Lett.2001, 3, 2543-2546.


Synthesis of a potential intermediate for pseudomonic acid b

Synthesis of a Potential Intermediate for Pseudomonic Acid B

Honda, T.; Kimura, N. Org. Lett.2002, 4, 4567-4570.


Enantioselective desymmetrisation of alkenes previous work

Enantioselective Desymmetrisation of Alkenes: Previous Work

1987, Schreiber:

1996, Landais:

1990, Ito:


Enantioselective desymmetrisation of alkenes previous work1

Enantioselective Desymmetrisation of Alkenes: Previous Work

1985, Whitesell:

1992, Mikami:

1994, Martin:


Enantioselective desymmetrisation of alkenes previous work2

Enantioselective Desymmetrisation of Alkenes: Previous Work

1998, Schrock and Hoveyda:


Preparation of cyclic amines through mo catalyzed asymmetric rcm

Preparation of Cyclic Amines Through Mo-Catalyzed Asymmetric RCM

Dolman, S. J.; Sattely, E. S.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 2002, 124, 6991-6997.


Enantioselective ru catalyzed rcm

Enantioselective Ru-Catalyzed RCM

Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett.2001, 3, 3225-3228.


Enantioselective ru catalyzed rcm1

Enantioselective Ru-Catalyzed RCM

Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett.2001, 3, 3225-3228.


Tandem catalytic asymmetric rom rcm

Tandem Catalytic Asymmetric ROM/RCM

Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc.2000, 122, 1828-1829.


Tandem catalytic asymmetric rom rcm1

Tandem Catalytic Asymmetric ROM/RCM

Weatherhead, G. S.; Ford, J. G.; Alexanian, E. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc.2000, 122, 1828-1829.


Desymmetrisation of meso bicyclic hydrazines by enantioselective hydroboration

Desymmetrisation of Meso Bicyclic Hydrazines by Enantioselective Hydroboration

Luna, A. P.; Ceschi, M. A.; Bonin, M.; Micouin, L.; Husson, H. P.; Gougeon, S.; Estenne-Bouhtou,

G.; Marabout, B.; Sevrin, M.; George, P. J. Org. Chem. 2002, 67, 3522-3524.


Desymmetrisation of meso bicyclic hydrazines by enantioselective hydroboration1

Desymmetrisation of Meso Bicyclic Hydrazines by Enantioselective Hydroboration

Luna, A. P.; Ceschi, M. A.; Bonin, M.; Micouin, L.; Husson, H. P.; Gougeon, S.; Estenne-Bouhtou,

G.; Marabout, B.; Sevrin, M.; George, P. J. Org. Chem. 2002, 67, 3522-3524.


Asymmetric synthesis of polyhydroxylated celastraceae sesquiterpene cores

Asymmetric Synthesis of Polyhydroxylated Celastraceae Sesquiterpene Cores

Spivey, A. C.; Woodhead, S. J.; Weston, M.; Andrews, B. I. Angew. Chem. Int. Ed. 2001, 40, 769-771.


Enantioselective desymmetrisation of meso decalin diallylic alcohols by zr based sae

Enantioselective Desymmetrisation of Meso-Decalin Diallylic Alcohols by Zr-Based SAE

Spivey, A. C.; Woodhead, S. J.; Weston, M.; Andrews, B. I. Angew. Chem. Int. Ed. 2001, 40, 769-771.


Enantioselective desymmetrisation of diols previous work

Enantioselective Desymmetrisation of Diols: Previous Work

1998, Oriyama:

1998, Fu:

1996, Trost:


Enantioselective desymmetrisation of diols previous work1

Enantioselective Desymmetrisation of Diols: Previous Work

1997, Fujioka:

1997, Harada:


Pd catalyzed enantioselective oxidation

Pd-Catalyzed Enantioselective Oxidation

Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475-7476.


Asymmetric oxidation of meso diols under photo irradiation

Asymmetric Oxidation of Meso-Diols under Photo-Irradiation

Shimizu, H.; Nakata, K.; Katsuki, T. Chem. Lett.2002, 1080-1081.


Enantioselective desymmetrisation of meso cyclic allylic bisdiethylphosphate

Enantioselective Desymmetrisation of Meso Cyclic Allylic Bisdiethylphosphate

Piarulli, U.; Daubos, P.; Claverie, C; Roux, M; Gennari, C. Angew. Chem. Int. Ed. 2003, 42, 234-236.


Pd catalyzed enantioselective ring opening with dialkylzinc

Pd-Catalyzed Enantioselective Ring Opening with Dialkylzinc

Lautens, M.; Renaud, J.-L.; Hiebert, S. J. Am. Chem. Soc. 2000, 122, 1804-1805.


Rh catalyzed enantioselective ring opening with organoboronic acids

Rh-Catalyzed Enantioselective Ring Opening with Organoboronic Acids

Lautens, M.; Dockendorff, C.; Fagnou, K.; Malicki, A. Org. Lett.2002, 4, 1311-1314.


Desymmetrisation of diols with a dinuclear zinc asymmetric catalyst

Desymmetrisation of Diols with a Dinuclear Zinc Asymmetric Catalyst

Trost, B. M.; Mino, T. J. Am. Chem. Soc. ASAP


Summary

Summary

  • Previous works on the enantioselective desymmetrisation have been introduced briefly according to different functional groups

  • Recent developments in the enantioselective desymmetrisation have been surveyed based on different functional groups

  • Recent applications of enantioselective desymmetrisation in natural products synthesis have been shown


Acknowledgement

Acknowledgement

Dr. Jeffrey Johnson

Johnson group


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