Journal
TETRAHEDRON LETTERS
Volume 54, Issue 15, Pages 2026-2028Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.02.020
Keywords
The HWE reaction; alpha,beta-Unsaturated nitriles; Z-Selective; Stereoselectivity; Aldehydes
Categories
Funding
- Ministry of Education, Culture, Sports, Science and Technology, Japan
- Grants-in-Aid for Scientific Research [25109521, 25410111, 25105719] Funding Source: KAKEN
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A new HWE reagent, (o-tBuC(6)H(4)O)(2)P(O)CH2CN (2e), reacts with various types of aldehydes to give Z-alpha,beta-unsaturated nitriles with 86% to >99% Z-selectivity. Especially, the reaction of 2e with bulkier aldehydes, both aromatic and aliphatic, gave the Z-olefins with extremely high selectivity. The combination of t-BuOK and 18-crown-6 (1 equiv) is the base of choice for aromatic aldehydes and t-BuOK is generally the base of choice for aliphatic aldehydes. (C)2013 Elsevier Ltd. All rights reserved.
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