通过级联共轭加成-缩合反应的有机催化不对称合成手性吡咯里嗪。
Organocatalytic asymmetric synthesis of chiral pyrrolizines by cascade conjugate addition-aldol reactions.
机构信息
Department of Chemistry, Kyungpook National University, Daegu 702-701, Republic of Korea.
出版信息
Org Lett. 2010 Oct 1;12(19):4352-5. doi: 10.1021/ol101811c.
PMID:20795732
Abstract
As the first N-centered heteroaromatic nucleophile for organocatalytic cascade reactions, pyrroles underwent the enantio- and diastereoselective organocatalytic cascade conjugate addition-aldol reactions of α,β-unsaturated aldehydes that afford the highly functionalized chiral pyrrolizines bearing three consecutive stereocenters in good yields, high enantioselectivities (90-98% ee), and excellent diastereoselectivities (>20:1 dr in all cases).
摘要
作为第一个 N 中心杂芳族亲核试剂，用于有机催化级联反应，吡咯经历了对映选择性和非对映选择性的有机催化级联共轭加成-缩合反应，与α，β-不饱和醛反应，以高产率、高对映选择性（90-98%ee）和优异的非对映选择性（所有情况下>20:1 dr）得到高度官能化的手性吡咯嗪，具有三个连续的立体中心。
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