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(+)‐Sparteine‐Mediated Substitution of o ‐Benzyl‐ N ‐pivaloylaniline with Ketones
Author(s) -
Ko Yi Kyung,
Im Chan,
Do Junghwan,
Park Yong Sun
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402110
Subject(s) - sparteine , chemistry , substitution (logic) , tetralin , derivative (finance) , ketone , medicinal chemistry , enantioselective synthesis , stereochemistry , organic chemistry , catalysis , computer science , financial economics , economics , programming language
The (+)‐sparteine‐mediated lithiation–substitution of o ‐benzyl‐ N ‐pivaloylaniline with various ketones was investigated. The obtained highly enantioenriched tertiary alcohols were used for the synthesis of alkenyl‐substituted products 12 and 13 as well as 3,3,4‐trisubstituted tetrahydroquinoline derivatives 22 – 24 . The reaction with α,β‐unsaturated ketones afforded highly enantioenriched 1,4‐addition products 28 – 33 and provided a protocol for the asymmetric synthesis of highly substituted tetralin derivative 34 .