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Rhodium‐Catalyzed Addition of Alkyltrifluoroborate Salts to Imines
Author(s) -
Lee Sumin,
Lee Woo Lim,
Yun Jaesook
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.201500295
Subject(s) - rhodium , chemistry , catalysis , hydride , potassium , organic chemistry , cyclooctadiene , medicinal chemistry , hydrogen
An efficient rhodium‐catalyzed addition of potassium alkyltrifluoroborate salts to imines is presented. In this reaction, secondary alkyltrifluoroborate salts were coupled with N ‐sulfonylimines in the presence of bis[(1,5‐cyclooctadiene)(hydroxy)rhodium] {[Rh(OH)(cod)] 2 } in good yields under mild reaction conditions, and the γ‐amino ester products could be converted to β,γ‐substituted lactams via cyclization. It was shown that the addition of enantiomerically enriched substrates to imines proceeded with excellent enantiospecificity and stereoretention without β‐hydride elimination.