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Enantioselective α‐Alkylation of Benzylideneamino tert ‐Butyl Malonates by Phase‐Transfer Catalysis
Author(s) -
Park Cheonhyoung,
Ha Min Woo,
Kim Byungsoo,
Hong Suckchang,
Kim Doyoung,
Park Yohan,
Kim Mihyun,
Lee Jae Kyun,
Lee Jeeyeon,
Park Hyeunggeun
Publication year - 2015
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.201500560
Subject(s) - chemistry , alkylation , enantioselective synthesis , catalysis , bromide , organic chemistry , hydrolysis , phase (matter) , combinatorial chemistry
A new enantioselective synthetic method for the synthesis of α,α‐dialkylmalonates with a quaternary carbon center was developed via α‐alkylation of prochiral malonates by phase‐transfer catalysis (PTC). Asymmetric α‐alkylation of benzylideneamino tert ‐butyl α‐methylmalonates under phase‐transfer catalytic conditions in the presence of ( S , S )‐3,4,5‐trifluorophenyl‐NAS bromide afforded the corresponding α,α‐dialkylmalonates in high yields (up to 97%) with excellent enantioselectivities (up to 98% ee ). The products were then selectively hydrolyzed to chiral malonic monoacids under basic, acidic, or catalytic hydrogenation conditions.