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. 2009 Apr 3;74(7):2798-803.
doi: 10.1021/jo9001504.

Vinylaluminum addition to sulfinimines (N-sulfinyl imines). Asymmetric synthesis of anti-alpha-alkyl beta-amino esters

Franklin A Davis  1 , Hui Qiu, Minsoo Song, Narendra V Gaddiraju
Affiliations

Vinylaluminum addition to sulfinimines (N-sulfinyl imines). Asymmetric synthesis of anti-alpha-alkyl beta-amino esters

Franklin A Davis et al. J Org Chem. .

Abstract

Addition of vinylaluminum NMO reagents to N-(p-toluenesufinyl)- and N-(2-methypropanesulfinyl)-derived sulfinimines gives N-sulfinyl aza-Morita-Baylis-Hillman products (dr = 7:1 to 12:1) that result from addition of the reagent from the least hindered direction. Hydrogenation of the aza-MBH adducts with a Rh(I) catalyst affords anti-alpha-substituted N-sulfinyl-beta-amino esters in good yield and high dr (10:1 to 21:1).

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Figures

Figure 1
Figure 1
Retrosynthetic approach to α-substituted N-sulfinyl β-amino esters.
Scheme 1
Scheme 1
Scheme 2
Scheme 2
Figure 2
Figure 2
Model for the addition of vinylaluminum to the si-face of (S)-(+)-3.
Scheme 3
Scheme 3
Scheme 4
Scheme 4
See this image and copyright information in PMC

References

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