Enantioselective α‐Alkylation of Benzylideneamino tert‐Butyl Malonates by Phase‐Transfer Catalysis. Issue 13 (10th September 2015)

• Record Type: Journal Article
• Authors: Park, Cheonhyoung; Ha, Min Woo; Kim, Byungsoo; Hong, Suckchang; Kim, Doyoung; Park, Yohan; Kim, Mi‐hyun; Lee, Jae Kyun; Lee, Jeeyeon; Park, Hyeung‐geun
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 13(2015)
• Page Start: 2841
• Page End: 2848
• Publication Date: 2015-09-10
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500560
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A new enantioselective synthetic method for the synthesis of α, α‐dialkylmalonates with a quaternary carbon center was developed <italic>via</italic> α‐alkylation of prochiral malonates by phase‐transfer catalysis (PTC). Asymmetric α‐alkylation of benzylideneamino <italic>tert</italic>‐butyl α‐methylmalonates under phase‐transfer catalytic conditions in the presence of (<italic>S</italic>, <italic>S</italic>)‐3, 4, 5‐trifluorophenyl‐NAS bromide afforded the corresponding α, α‐dialkylmalonates in high yields (up to 97%) with excellent enantioselectivities (up to 98% <italic>ee</italic>). The products were then selectively hydrolyzed to chiral malonic monoacids under basic, acidic, or catalytic hydrogenation conditions.</p> <p> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgj2n0t63mn" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </p> </abstract>