Palladium-Catalyzed Asymmetric Synthesis of 2-Alkynyl Oxacycles

被引:27
作者
Daniels, David S. B. [1 ]
Thompson, Amber L. [1 ]
Anderson, Edward A. [1 ]
机构
[1] Univ Oxford, Dept Chem, Oxford OX1 3TA, England
基金
英国工程与自然科学研究理事会;
关键词
alkynes; asymmetric synthesis; cyclization; oxygen heterocycles; palladium; ALKYNYL CYCLIC CARBONATES; STEREOSELECTIVE-SYNTHESIS; CYCLIZATION; HETEROCYCLES; ALCOHOLS; ALLENES;
D O I
10.1002/anie.201105720
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Oxyacetylene: Unusual palladium-catalyzed cyclizations of cyclic and acyclic propargylic carbonates give 2-alkynyl oxacycles. The reactions proceed with very high stereoselectivity for both syn- and anti-disubstituted furans and pyrans, and with exceptional regioselectivity. In addition, two-directional cyclizations of bis-propargylic carbonate substrates yield bifurans with complete stereocontrol for all diastereomers. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:11506 / 11510
页数:5
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