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Titanated Methoxyallene as Novel Homoaldol Equivalent for Diastereoselective Additions to Chiral Amino Aldehydes
Author(s) -
Hormuth Stephan,
Reissig HansUlrich,
Dorsch Dieter
Publication year - 1993
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199314491
Subject(s) - hydrolysis , selectivity , derivative (finance) , titanium , chemistry , block (permutation group theory) , aldehyde , organic chemistry , medicinal chemistry , catalysis , mathematics , combinatorics , financial economics , economics
The versatile building block, methoxyallene reveals another a new facet: The titanium derivative 1 derived from it reacts with aldehydes at the γ position. Thus the methoxyalkynes anti ‐3 arise with high anti ‐selectivity on reaction of 1 with α‐ N,N ‐dibenzylamino aldehydes 2 . These activated carboxylic acid derivatives can be transformed into the homostatine lactones anti ‐ 4 by hydrolysis. R CH 3 , CH 2 Ph, CH 2 CHMe 2 .