Premium
Stereo‐ and Regiochemical Divergence in the Substitution of a Lithiated Alk‐1‐en‐3‐yn‐2‐yl Carbamate: Synthesis of Highly Enantioenriched Vinylallenes or Alk‐3‐en‐5‐yn‐1‐ols
Author(s) -
Bou Chedid Roland,
Brümmer Michael,
Wibbeling Birgit,
Fröhlich Roland,
Hoppe Dieter
Publication year - 2007
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/anie.200604978
Subject(s) - stereoselectivity , carbamate , chemistry , electrophile , substitution (logic) , lithium (medication) , inversion (geology) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , computer science , programming language , biology , paleontology , structural basin , endocrinology
Alternative outcomes . The regio‐ and stereoselectivity of the hydroxyalkylation of a lithiated alk‐1‐en‐3‐yn‐2‐yl carbamate such as ( S )‐ 1 can be controlled simply for the synthesis of highly enantioenriched vinylallenes 2 . Alternatively, lithium–titanium exchange proceeds with inversion of configuration, and addition of carbonyl electrophiles produces enantioenriched homoaldol products such as ( S , Z )‐ 3 (see scheme, Cb=carbamoyl).