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Highly Regio‐ and Stereoselective Iodohydroxylation of Non‐ Heteroatom‐Substituted Allenes: An Efficient Synthesis of 4‐[3′‐Hydroxy‐2′‐iodoalk‐1′( Z )‐enyl]‐2(5 H )‐furanone Derivatives
Author(s) -
Gu Zhenhua,
Deng Youqian,
Shu Wei,
Ma Shengming
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700181
Subject(s) - chemistry , stereoselectivity , heteroatom , steric effects , furan , stereochemistry , regioselectivity , ring (chemistry) , organic chemistry , catalysis
An efficient protocol for the highly regio‐ and stereoselective synthesis of 4‐(3′‐hydroxy‐2′‐iodoalk‐1′( Z )‐enyl)furan‐2(5 H )‐one derivatives via selective iodohydroxylation of non‐heteroatom‐substituted allenes, i.e., 4‐allenyl‐2(5 H )furanones, has been developed. The regio‐ and stereoselectivity of this reaction may be controlled by the electronic and steric effects of the furanone ring.