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Enantioselective Allenylation of Aldehydes via Brønsted Acid Catalysis
Author(s) -
Wang Mengzhou,
Khan Shahriar,
Miliordos Evangelos,
Chen Ming
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801080
Subject(s) - enantioselective synthesis , chemistry , moiety , pinacol , phosphoric acid , catalysis , asymmetric induction , brønsted–lowry acid–base theory , organic chemistry , combinatorial chemistry
An enantioselective allenylation of aldehydes catalyzed by a chiral, nonracemic phosphoric acid was reported. Under the developed conditions, 1,1′‐disubstituted allenic alcohols were obtained in 64–98% yields with 88–99% ee. Computational studies were conducted to probe the origin of asymmetric induction. Mechanistic studies suggest that the pinacol moiety of the propargylboronate is critical to the enantioselectivity of the reaction that was supported by experimental data.