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Stereocontrolled Synthesis of Paraconates from β‐Lactones; Stereochemistry of Electrophilic Additions to Endocyclic Paraconate‐Enolates
Author(s) -
Mulzer Johann,
Chucholowski Alexander
Publication year - 1986
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198606551
Subject(s) - electrophile , steric effects , alkyl , chemistry , halide , adduct , aryl , stereoselectivity , addition reaction , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The addition of electrophiles to paraconate‐enolates is controlled purely sterically and not stereoelectronically . This surprising result was found upon reaction of the enolates 1 with alkyl halides and aldehydes, whereby the adducts 2 and 3 are formed stereoselectively in good yields. R 1 , R 2 , R 3 alkyl, aryl.