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. 2009 Dec 23;131(50):18034-5.
doi: 10.1021/ja908075u.

Rhodium-catalyzed enantioselective cyclopropanation of olefins with N-sulfonyl 1,2,3-triazoles

Stepan Chuprakov  1 , Sen Wai Kwok, Li Zhang, Lukas Lercher, Valery V Fokin
Affiliations

Rhodium-catalyzed enantioselective cyclopropanation of olefins with N-sulfonyl 1,2,3-triazoles

Stepan Chuprakov et al. J Am Chem Soc. .

Abstract

N-Sulfonyl 1,2,3-triazoles readily form rhodium(II) azavinyl carbenes, which react with olefins to produce cyclopropanes with excellent diastereo- and enantioselectivity and in high yield.

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Figures

Figure 1
Figure 1
Rh(II) carboxylates for asymmetric cyclopropanation.
Scheme 1
Scheme 1
Enantioselective Cyclopropanation with 1,2,3-Triazoles: Scope of Olefinsa aUnless specified otherwise, all reactions were carried out on 0.5 mmol scale with 1.2 equiv of olefin and under ambient atmosphere; bdetermined by 1H NMR of the crude reaction mixture; c2.0 equiv. of alkene were used.
Scheme 2
Scheme 2
Enantioselective Cyclopropanation of Styrene with N-Methanesulfonyl 1,2,3-Triazoles a All reactions were carried out in 0.5 mmol scale with 1.2 equiv of olefin, and under ambient atmosphere. b Determined by 1H NMR of the crude reaction mixture.
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References

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    1. For recent reviews, see: Davies HML, Manning JR. Nature. 2008;451:417. Doyle MP. In: Modern Rhodium-Catalyzed Organic Reactions. Evans PA, editor. NY: Wiley; 2005. pp. 341–355. Davies HML, Beckwith REJ. Chem. Rev. 2003;103:2861. Lebel H, Marcoux J-F, Molinaro C, Charette AB. Chem. Rev. 2003;103:977.

    1. For related transformations involving (2-pyrydyl)-carbenoids, see: Davies HML, Townsend RJ. J. Org. Chem. 2001;66:6595. Chuprakov S, Gevorgyan V. Org. Lett. 2007;9:4463.

    1. α-Diazoimines are known to exist in cyclic 1,2,3-triazole form, except for those bearing strong electron-withdrawing group at N-1: Dimroth O. Ann. 1909;364:183. Gilchrist TL, Gymer GE. Adv. Heterocycl. Chem. 1974;16:33.

    1. Raushel J. Ph.D. Dissertation (The Scripps Research Intitute). Diss. Abstr. Int., B. 8. Vol. 69. 2009. p. 4763. Cassidy MP, Raushel J, Fokin VV. Angew. Chem. Int. Ed. 2006;45:3154. See also ref.

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