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Highly Stereoselective Synthesis of Tertiary Propargylic Centers and Their Isomerization to Enantiomerically Enriched Allenes
Author(s) -
García Ruano José Luis,
Marzo Leyre,
Marcos Vanesa,
Alvarado Cuauhtémoc,
Alemán José
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201201607
Subject(s) - stereoselectivity , isomerization , lithium (medication) , chemistry , center (category theory) , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , crystallography , psychology , psychiatry
Center of attention : A new approach for the synthesis of enantiomerically enriched allenes by isomerization of 2‐ p ‐tolylsulfinylphenyl propargylic derivatives is presented, which in turn are prepared by reaction of sulfinylated lithium benzylcarbanions with arylsulfonylacetylenes (see scheme). The high control of stereoselectivity in both steps is exerted by the sulfinyl group.