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Highly Enantioselective α Alkylation of Aldehydes with 1,3‐Benzodithiolylium Tetrafluoroborate: A Formal Organocatalytic α Alkylation of Aldehydes by the Carbenium Ion
Author(s) -
Gualandi Andrea,
Emer Enrico,
Capdevila Montse Guiteras,
Cozzi Pier Giorgio
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201102562
Subject(s) - alkylation , chemistry , carbenium ion , carbocation , carbanion , synthon , deprotonation , electrophile , enantioselective synthesis , combinatorial chemistry , hydride , cationic polymerization , organic chemistry , catalysis , ion , hydrogen
A formal formyl : The organocatalytic stereoselective addition of formyl equivalents to aldehydes (see scheme) tolerates a large variety of functional groups to afford products with high enantioselectivity (92–97 % ee ) and good yields (up to 95 %). The benzodithiol group can be easily removed with Raney Ni or metalated with n BuLi, thus giving access to a methyl group or to a wide range of useful intermediates.