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Kinder RE, Widenhoefer RA. Rhodium-catalyzed asymmetric cyclization/hydroboration of 1,6-enynes. Org Lett. 2006;8(10):1967-9doi: 10.1021/ol052986t.
Kinder, R. E., & Widenhoefer, R. A. (2006). Rhodium-catalyzed asymmetric cyclization/hydroboration of 1,6-enynes. Organic letters, 8(10), 1967-9. https://doi.org/10.1021/ol052986t
Kinder, Robert E, and Widenhoefer, Ross A. "Rhodium-catalyzed asymmetric cyclization/hydroboration of 1,6-enynes." Organic letters vol. 8,10 (2006): 1967-9. doi: https://doi.org/10.1021/ol052986t
Kinder RE, Widenhoefer RA. Rhodium-catalyzed asymmetric cyclization/hydroboration of 1,6-enynes. Org Lett. 2006 May 11;8(10):1967-9. doi: 10.1021/ol052986t. PMID: 16671758.
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Org Lett. 2006 May 11;8(10):1967-9. doi: 10.1021/ol052986t.

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

Organic letters

Robert E Kinder, Ross A Widenhoefer

Affiliations

  1. PM Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708-0346, USA.

PMID: 16671758 DOI: 10.1021/ol052986t

Abstract

[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.

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