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Addition of Enantioenriched γ ‐Oxygenated Allylic Stannanes to N ‐Acyl Iminium Intermediates: A New Synthesis of syn ‐Amino Alcohol Derivatives
Author(s) -
Marshall James A.,
Gill Kevin,
Seletsky Boris M.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000303)39:5<953::aid-anie953>3.0.co;2-i
Subject(s) - chemistry , allylic rearrangement , substituent , iminium , lewis acids and bases , medicinal chemistry , allylic alcohol , ton , alcohol , organic chemistry , catalysis , fishery , biology
An ortho ‐methoxybenzyl substituent is the key to high diastereoselectivities in a novel synthesis of syn ‐ β ‐amino alcohols from N ‐benzyl‐ N ‐carbethoxyiminium salts and γ ‐oxygenated allylic stannanes (the reaction is promoted by the Lewis acid BF 3 ⋅OEt 2 ; see scheme). Enantioselectivites of over 95 % and syn : anti ratios of greater than 95:5 were achieved. Ar= o ‐MeOC 6 H 4 , MOM=methoxymethyl.