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Synthesis of Highly Functionalized Propargylic Alcohols: Direct Addition of Epoxy Acetylides to Aldehydes and Ketones
Author(s) -
HoffmannRöder Anja,
Krause Norbert
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200210)85:10<3176::aid-hlca3176>3.0.co;2-7
Subject(s) - chemistry , lithium diisopropylamide , regioselectivity , epoxide , nucleophile , silylation , lithium (medication) , nucleophilic addition , organic chemistry , functional group , halide , aldehyde , molecule , addition reaction , catalysis , deprotonation , medicine , ion , endocrinology , polymer
Direct nucleophilic addition of terminal alkynes comprising an epoxy group to aldehydes and ketones is reported with BuLi or lithium diisopropylamide for the generation of the corresponding lithium acetylides. This alkynylation reaction tolerates a wide variety of different functional groups ( e.g. , alcohols, silyl ethers, halides, double bonds) in the carbonyl compound, as well as in the acetylenic nucleophile, and furnishes highly functionalized propargylic alcohols in good‐to‐excellent yields. The method is particularly useful for the regioselective introduction of an epoxide function into multiply unsaturated target molecules.