Highly Enantioselective α Alkylation of Aldehydes with 1,3‐Benzodithiolylium Tetrafluoroborate: A Formal Organocatalytic α Alkylation of Aldehydes by the Carbenium Ion | Zendy

Gualandi Andrea | Zendy; Emer Enrico | Zendy; Capdevila Montse Guiteras | Zendy; Cozzi Pier Giorgio | Zendy

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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.

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