Lewis acid-catalysed aza-Diels-Alder versus Mannich reactions of N-diethyl phosphoryl imino dienophiles with oxygenated dienes and application of a chiral lewis acid

被引：9
作者：
Di Bari, L
Guillarme, S
Hermitage, S
Howard, JAK
Jay, DA
Pescitelli, G
Whiting, A
Yufit, DS
机构：
[1] Univ Durham, Sci Labs, Dept Chem, Durham DH1 3LE, England
[2] Dipartimento Chim & Chim Ind, I-56126 Pisa, Italy
[3] GlaxoSmithKline, Med Res Ctr, Stevenage SG1 2NY, Herts, England
来源：
SYNLETT | 2004年 / 04期
关键词：
heterodienophile; Diels-Alder reaction; Mannich reaction; asymmetric induction;
D O I：
10.1055/s-2004-817742
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Phosphoryl imines react with oxygenated dienes in the presence of Lewis acids to provide either the formal aza-Diels-Alder adduct, or the acyclic Mannich-type addition product, depending upon the catalyst and work up used, which is in agreement with the hypothesis that these reactions are mediated by zwitterionic Lewis acid-complex intermediates, rather than a concerted cyclo-addition transition-state followed by hydrolytic ring opening. Stoichiometric asymmetric induction can be achieved using a zinc(II)binol complex, producing up 77% ee.
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收藏
页码：708 / 710
页数：3
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