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Stereocontrolled Synthesis of Highly Functionalized Quaternary Carbon Centers: A Route to α‐Substituted Serines
Author(s) -
Ariza Xavier,
Cornellà Josep,
FontBardia Mercè,
Garcia Jordi,
Ortiz Jordi,
Sánchez Carolina,
Solans Xavier
Publication year - 2009
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.200900609
Subject(s) - hydroboration , allene , quaternary carbon , enantioselective synthesis , tandem , aldehyde , chemistry , combinatorial chemistry , carbon fibers , stereochemistry , organic chemistry , catalysis , computer science , materials science , composite number , composite material , algorithm
Three in a row! Highly functionalized quaternary amino polyols with three consecutive asymmetric carbon centers have been prepared through tandem hydroboration of allene 1 and addition to an aldehyde (see scheme; Cy=cyclohexyl, TBDPS= tert ‐butyldiphenylsilyl, Ts=4‐toluenesulfonyl). This one‐pot process provides access to advanced intermediates for the enantioselective synthesis of α‐substituted serines.