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Vicinal Functionalization of N ‐Alkoxyenamines: Tandem Umpolung Phenylation–Nucleophilic Addition Reaction Sequence
Author(s) -
Sato Shohei,
Takeda Norihiko,
Miyoshi Tetsuya,
Ueda Masafumi,
Miyata Okiko
Publication year - 2015
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.201500308
Subject(s) - chemistry , umpolung , vicinal , nucleophile , surface modification , reagent , organic chemistry , bromide , nucleophilic addition , cyanide , amine gas treating , combinatorial chemistry , catalysis
The vicinal functionalization of N ‐alkoxyenamines, derived in situ from aldehydes and isoxazolidines, has been achieved with the formation of two new carbon–carbon bonds by utilizing an organo‐aluminum reagent and subsequent allylmagnesium bromide or tributyltin cyanide as external carbon‐centered nucleophiles. By changing the second carbon nucleophile, various amine derivatives were obtained in good yields.