布朗斯台德酸催化的区域选择性氮杂-费里尔反应：一种合成α-(N-叔丁氧羰基-2-吡咯烷基)醛的新方法。

Brønsted acid catalyzed regioselective aza-Ferrier reaction: a novel synthetic method for alpha-(N-Boc-2-pyrrolidinyl) aldehydes.

作者信息

Tayama Eiji, Otoyama Seijun, Isaka Wataru

机构信息

Graduate School of Science and Technology, Niigata University, Niigata 950-2181, Japan.

出版信息

Chem Commun (Camb). 2008 Sep 21(35):4216-8. doi: 10.1039/b806492j. Epub 2008 Jul 15.

DOI:10.1039/b806492j

PMID:18802534

Abstract

The 1,4-elimination reaction of (Z)-N-Boc-2-(4-methoxy-2-alkenyloxy)pyrrolidines is shown to proceed with high (1E,3E)-stereoselectivity to afford N-Boc-2-(1,3-dienyloxy)pyrrolidines; the Brønsted acid catalyzed aza-Ferrier reaction of the N-Boc-2-(1,3-dienyloxy)pyrrolidines (3) provides alpha-(N-Boc-2-pyrrolidinyl) aldehydes in excellent yields with high alpha-regioselectivities.

摘要

(Z)-N-叔丁氧羰基-2-(4-甲氧基-2-烯基氧基)吡咯烷的1,4-消除反应显示出以高(1E,3E)-立体选择性进行，生成N-叔丁氧羰基-2-(1,3-二烯基氧基)吡咯烷；N-叔丁氧羰基-2-(1,3-二烯基氧基)吡咯烷(3)的布朗斯特酸催化氮杂-Ferrier反应以优异的产率和高α-区域选择性提供α-(N-叔丁氧羰基-2-吡咯烷基)醛。