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

Vinylaluminum addition to sulfinimines (N-sulfinyl imines). Asymmetric synthesis of anti-alpha-alkyl beta-amino esters.
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乙烯基铝与亚磺酰亚胺(N-亚磺酰亚胺)相加。

DOI:
10.1021/jo9001504
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发表时间:
2009
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Gaddiraju,NarendraV
Gaddiraju,NarendraV
中科院分区:
--
文献类型:
--
作者:
Davis,FranklinA;Qiu,Hui;Song,Minsoo;Gaddiraju,NarendraV

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Addition of vinylaluminum NMO reagents toN-(p-toluenesufinyl)- andN-(2-methypropanesulfinyl)-derived sulfinimines givesN-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 affordsanti-α-substitutedN-sulfinyl-β-amino esters in good yield and high dr (10:1 to 21:1).