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Synthesis of α‐Hydroxyallenes by Copper‐Catalyzed S N 2′ Substitution of Propargylic Dioxolanones
Author(s) -
Tang Xiaoping,
Woodward Simon,
Krause Norbert
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900226
Subject(s) - chemistry , catalysis , copper , reagent , nucleophilic substitution , substitution (logic) , substitution reaction , nucleophile , combinatorial chemistry , grignard reagent , medicinal chemistry , primary (astronomy) , organic chemistry , computer science , programming language , physics , astronomy
A new catalytic method for the synthesis of α‐hydroxyallenes is described. Efficient S N 2′ substitution of propargylic dioxolanones has been achieved with a copper(I)/P(OBu) 3 catalyst using Grignard reagents as the nucleophiles. The reaction tolerates a wide variety of propargylic dioxolanones, the corresponding primary and secondary α‐hydroxyallenes are obtained in good to excellent yields and excellent diastereoselectivity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)