Premium
Microwave‐Assisted Rhodium‐Complex‐Catalyzed Cascade Decarbonylation and Asymmetric Pauson–Khand‐Type Cyclizations
Author(s) -
Lee Hang Wai,
Lee Lai Na,
Chan Albert S. C.,
Kwong Fuk Yee
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800272
Subject(s) - decarbonylation , chemistry , enantioselective synthesis , rhodium , cyclopentenone , carbonylation , catalysis , aldehyde , pauson–khand reaction , hydroformylation , formate , cascade , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry , carbon monoxide , chromatography
Microwave‐assisted Rh–diphosphane‐complex‐catalyzed dual catalysis is reported. This cooperative process provides [2+2+1] cycloadducts by sequential decarbonylation of aldehyde or formate and carbonylation of enynes within a short period of time. Various O‐, N‐, and C‐tethered enynes were transformed into the corresponding products in good yields. The first enantioselective version of this microwave‐accelerated cascade cyclization was realized. In the presence of chiral Rh‐( S )‐bisbenzodioxanPhos complex, the cyclopentenone products were achieved with ee values up to 90 %. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)