Asymmetric Multicomponent Domino Reactions and Highly Enantioselective Conjugated Addition of Thiols to ,<img src="http://pubs.acs.o
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- 作者：Mauro Marigo ; Tobias Schulte ; Johan Franzé ; n ; and Karl Anker J<img src="http ; //pubs.acs.org/images/gifchars/oslash.gif" border="0">rgensen
- 刊名：Journal of the American Chemical Society
- 出版年：2005
- 出版时间：November 16, 2005
- 年：2005
- 卷：127
- 期：45
- 页码：15710 - 15711
- 全文大小：41K
- 年卷期：v.127,no.45(November 16, 2005)
- ISSN：1520-5126
文摘
An organocatalytic asymmetric multicomponent domino and a conjugated addition reaction to <IMG SRC="/images/gifchars/alpha.gif" BORDER=0>,
-unsaturated aldehydes are presented. The development is based, first, on an organocatalyzed highly enantioselective nucleophilic thiol addition to the -carbon atom in the iminium ion intermediate, followed by an electrophilic amination of the 
-carbon atom to the enamine intermediate. The multicomponent reactions proceed to give enantiopure amino-thiols in moderate to good yields. Furthermore, the organocatalyzed thiol addition to ,-unsaturated aldehydes takes place in good yields and excellent enantioselectivities.
-unsaturated aldehydes are presented. The development is based, first, on an organocatalyzed highly enantioselective nucleophilic thiol addition to the -carbon atom in the iminium ion intermediate, followed by an electrophilic amination of the -carbon atom to the enamine intermediate. The multicomponent reactions proceed to give enantiopure amino-thiols in moderate to good yields. Furthermore, the organocatalyzed thiol addition to ,-unsaturated aldehydes takes place in good yields and excellent enantioselectivities.