Title: | Boron Tribromide-Assisted Chiral Phosphoric Acid Catalysts for Enantioselective [2+2] Cycloaddition |
Author(s): | Sakamoto T; Mochizuki T; Goto Y; Hatano M; Ishihara K; |
Address: | "Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan" |
ISSN/ISBN: | 1861-471X (Electronic) 1861-471X (Linking) |
Abstract: | "BBr(3) -assisted chiral phosphoric acid catalysts for enantioselective [2+2] cycloaddition were developed. The reactions of phenyl vinyl sulfide with alpha-substituted acroleins proceeded, and the corresponding [2+2] cycloadducts were obtained with high enantioselectivity. In particular, the [2+2] cycloadduct obtained from methacrolein is a synthetically useful optically active cyclobutane, which could be transformed to a key intermediate for (+)-frontalin, a pheromone of Asian elephants" |
Keywords: | [2+2] cycloaddition boron Lewis acid chiral Bronsted acid catalyst cyclobutane phosphoric acid; |
Notes: | "PubMed-not-MEDLINESakamoto, Tatsuhiro Mochizuki, Takuya Goto, Yuta Hatano, Manabu Ishihara, Kazuaki eng JP17H03054/Japan Society for the Promotion of Science/ JP15H05755/Japan Society for the Promotion of Science/ JP15H05810/Japan Society for the Promotion of Science/ Germany 2018/04/01 Chem Asian J. 2018 Sep 4; 13(17):2373-2377. doi: 10.1002/asia.201800351. Epub 2018 Apr 30" |