Rhodium-catalyzed asymmetric cyclization/hydroboration of 1,6-enynes.

Journal Article (Journal Article)

[reaction: see text] Reaction of enyne 1 with catecholborane catalyzed by a 1:1 mixture of [Rh(COD)(2)](+)SbF(6)(-) and (S)-BINAP (5 mol %) followed by Pd-catalyzed arylation with p-IC(6)H(4)CF(3) gave benzylidenecyclopentane 5 in 65% yield with 88% ee. Rhodium-catalyzed asymmetric cyclization/hydroboration followed either by Pd-catalyzed arylation or by oxidation was applied to the synthesis of a number of chiral, nonracemic carbocycles and heterocycles.

Full Text

Duke Authors

Cited Authors

  • Kinder, RE; Widenhoefer, RA

Published Date

  • May 2006

Published In

Volume / Issue

  • 8 / 10

Start / End Page

  • 1967 - 1969

PubMed ID

  • 16671758

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol052986t

Language

  • eng