INSIGHT INTO RH(I)-CATALYZED CYCLIZATION OF 6-OCTEN-1-ALS WITH A CHIRAL PROTECTING GROUP

Authors
KOGA I FUNAKOSHI K MATSUDA A SAKAI K
Citation
I. Koga et al., INSIGHT INTO RH(I)-CATALYZED CYCLIZATION OF 6-OCTEN-1-ALS WITH A CHIRAL PROTECTING GROUP, Tetrahedron : asymmetry, 4(8), 1993, pp. 1857-1868
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
4
Issue
8
Year of publication
1993
Pages
1857 - 1868
Database
ISI
SICI code
0957-4166(1993)4:8<1857:IIRCO6>2.0.ZU;2-C
Abstract
Rh(I)(Wilkinson )[ClRh(PPh3)3]-catalyzed cyclization of 6-octen-1-als with a chiral protecting group at the C2-position afforded only cis-cy clohexanol derivatives, and in the case of C4-position yielded a mixtu re of cis and trans cyclohexanol. These findings were remarkably diffe rent from the case of the C3-position, in which the trans cyclohexanol derivative was obtained. Wilkinson's complex acts as [ClRh(PPh3)3] a Lewis acid, and this bulkier Lewis acid affords higher diastereoselect ivity. Rh(I)-catalyzed cyclization of 6-octen-1-al derivatives is not affected by chiral ligands.