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Stereoselective Synthesis of syn ‐β‐Amino Propargylic Ethers: Application to the Asymmetric Syntheses of (+)‐β‐Conhydrine and (−)‐Balanol
Author(s) -
Louvel Julien,
Chemla Fabrice,
Demont Emmanuel,
Ferreira Franck,
PérezLuna Alejandro,
Voituriez Arnaud
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100333
Subject(s) - enantiopure drug , chemistry , stereoselectivity , alcohol , combinatorial chemistry , stereochemistry , enantioselective synthesis , organic chemistry , catalysis
The stereoselective synthesis of syn ‐β‐amino propargylic ethers by the addition of racemic lithio 3‐(methoxymethoxy)allenylcuprates, and more particularly (cyano) and (mesityl)cuprates, to enantiopure chiral N‐tert ‐butylsulfinylimines is reported. The scope and limitations of the reaction is studied. The usefulness of the methodology for the synthesis of compounds having a syn ‐1,2‐amino alcohol unit is shown through the development of the asymmetric syntheses of (+)‐β‐conhydrine and of an advanced intermediate of (−)‐balanol.