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The Simultaneous In‐Situ Generation of Aldehydes and Phosphorus Ylides: A Convenient Multi‐Step One‐Pot Olefination Protocol
Author(s) -
Wang Qian,
Wei Hengxu,
Schlosser Manfred
Publication year - 1999
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/(sici)1099-0690(199912)1999:12<3263::aid-ejoc3263>3.0.co;2-u
Subject(s) - chemistry , reagent , in situ , lithium (medication) , nucleophile , dimethylformamide , wittig reaction , isomerization , organic chemistry , phosphorus , condensation , tetrahydrofuran , decomposition , combinatorial chemistry , catalysis , medicine , physics , solvent , thermodynamics , endocrinology
The lithium α‐(dimethylamino)alkoxides resulting from the nucleophilic addition of an organolithium reagent to N , N ‐dimethylformamide are basic enough to deprotonate alkyltriphenylphosphonium salts suspended in tetrahydrofuran. The aldehydes liberated by the spontaneous decomposition of the resulting α‐amino alcohols (hemiaminals) undergo a Wittig reaction with the simultaneously generated phosphorus ylides to afford olefins in excellent overall yields. This in situ method offers the unique advantage in its applicability to labile aldehydes which otherwise would become prey to ( Z/E )‐isomerization or self‐condensation processes.