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Wittig Rearrangements of (Heteroaryl)alkyl Propargyl Ethers − Synthesis of Allenic and Propargylic Alcohols
Author(s) -
Florio Saverio,
Granito Catia,
Ingrosso Giovanni,
Troisi Luigino
Publication year - 2002
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 - 10.1002/1099-0690(200210)2002:20<3465::aid-ejoc3465>3.0.co;2-t
Subject(s) - chemistry , propargyl , wittig reaction , electrophile , alkyl , organic chemistry , medicinal chemistry , catalysis
(Heteroaryl)alkyl propargyl ethers have been synthesized and treated with n BuLi in THF at −78 °C. The resulting α‐ or α′‐lithio derivatives could be trapped with iodomethane, affording the corresponding α‐ or α′‐methylated products. Treatment in the absence of an external electrophile resulted either in allenic alcohols or in propargylic alcohols, or in mixtures of both compounds, probably arising from competing [1,2]‐ and [2,3]‐Wittig rearrangements, in varying ratios. A high anti diastereoselectivity was observed in the propargylic alcohols produced. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)