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Enantioselective Synthesis of Cyclopentadienes by Gold(I)‐ Catalyzed Cyclization of 1,3‐Dien‐5‐ynes
Author(s) -
Sanjuán Ana M.,
GarcíaGarcía Patricia,
FernándezRodríguez Manuel A.,
Sanz Roberto
Publication year - 2013
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.201300448
Subject(s) - stereocenter , chemistry , enantioselective synthesis , catalysis , cycloaddition , enantiomer , enantiomeric excess , combinatorial chemistry , organic chemistry , stereochemistry
An asymmetric synthesis of elusive chiral cyclopentadienes has been developed by gold(I)‐catalyzed alkoxycyclization of 1,3‐dien‐5‐ynes. The application of these substrates in completely diastereoselective Diels–Alder cycloaddition reactions, which can be carried out in one pot from achiral 1,3‐dien‐5‐ynes, allows the preparation of highly functionalized products bearing five stereogenic centers with high enantiomeric excesses.