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Enantioselective Gold(I)‐Catalyzed Intramolecular (4+3) Cycloadditions of Allenedienes
Author(s) -
Alonso Isaac,
Faustino Hélio,
López Fernando,
Mascareñas José L.
Publication year - 2011
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.201105815
Subject(s) - enantioselective synthesis , intramolecular force , allene , cycloaddition , phosphoramidite , catalysis , chemistry , combinatorial chemistry , stereochemistry , computer science , organic chemistry , dna , biochemistry , oligonucleotide
Allene‐tethered dienes ( 1 ) undergo an intramolecular and highly enantioselective (4+3) cycloaddition when treated with suitable chiral phosphoramidite/gold(I) catalysts (see scheme; Ar=9‐anthracenyl). The reactions provide synthetically relevant [5.3.0] and [5.4.0] fused bicyclic systems 2 with good yields, complete diastereocontrol, and excellent enantioselectivities.