Premium
Lewis Base‐Catalyzed Addition of Trialkylaluminum Compounds to Epoxides
Author(s) -
Schneider Christoph,
Brauner Jörg
Publication year - 2001
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 - 10.1002/1099-0690(200112)2001:23<4445::aid-ejoc4445>3.0.co;2-u
Subject(s) - chemistry , lewis acids and bases , epoxide , alkylation , regioselectivity , nucleophile , catalysis , reagent , organic chemistry , combinatorial chemistry
A novel concept for catalytic epoxide alkylation has been developed. Lewis bases like phosphanes, arsanes, stibanes, and sulfides were found to catalyze the alkylation of symmetrical epoxides with trialkylaluminum compounds very effectively at a 5 mol % level. Cyclic as well as acyclic epoxides were readily alkylated in good yields. In reactions with terminal epoxides a significant enhancement of rate and/or regioselectivity was noted in the Lewis base‐catalyzed process. Coordination of the Lewis base to the Lewis acidic aluminum reagent was proved by 27 Al and 31 P NMR spectroscopy and is proposed to form a more nucleophilic alkylating agent.