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Asymmetric Hydrogenation of β‐Keto Sulfonamides and β‐Keto Sulfones with a Chiral Cationic Ruthenium Diamine Catalyst
Author(s) -
Huang XiaoFei,
Zhang ShaoYun,
Geng ZhiCong,
Kwok ChunYuen,
Liu Peng,
Li HaiYan,
Wang XingWang
Publication year - 2013
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.201300331
Subject(s) - chemistry , asymmetric hydrogenation , ruthenium , kinetic resolution , catalysis , cationic polymerization , sulfonamide , phosphine , optically active , organic chemistry , diamine , enantioselective synthesis , noyori asymmetric hydrogenation , combinatorial chemistry
Optically active β‐hydroxy sulfonamides and β‐hydroxy sulfones are very important building blocks for the preparation of bioactive compounds and pharmaceuticals. In this work, a highly efficient asymmetric hydrogenation of β‐keto sulfonamides and β‐keto sulfones has been developed using the phosphine‐free chiral ruthenium complex Ru(OTf)(TsDPEN)(η 6 ‐ p ‐cymene) as the catalyst, to afford the corresponding β‐hydroxy sulfonamides and β‐hydroxy sulfones in high yields with excellent optical purities. In addition, a cascade asymmetric hydrogenation/dynamic kinetic resolution (DKR) of racemic cyclic β‐keto sulfonamides and β‐keto sulfones was also realized using the same catalyst, to give the corresponding chiral cyclic β‐hydroxy sulfonamides and β‐hydroxy sulfones in good yields with excellent enantio‐ and diastereoselectivities.