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Shono T, Harada T. Catalytic enantioselective synthesis of secondary allylic alcohols from terminal alkynes and aldehydes via 1-alkenylboron reagents. Org Lett. 2010;12(22):5270-3doi: 10.1021/ol1023213.
Shono, T., & Harada, T. (2010). Catalytic enantioselective synthesis of secondary allylic alcohols from terminal alkynes and aldehydes via 1-alkenylboron reagents. Organic letters, 12(22), 5270-3. https://doi.org/10.1021/ol1023213
Shono, Takashi, and Harada, Toshiro. "Catalytic enantioselective synthesis of secondary allylic alcohols from terminal alkynes and aldehydes via 1-alkenylboron reagents." Organic letters vol. 12,22 (2010): 5270-3. doi: https://doi.org/10.1021/ol1023213
Shono T, Harada T. Catalytic enantioselective synthesis of secondary allylic alcohols from terminal alkynes and aldehydes via 1-alkenylboron reagents. Org Lett. 2010 Nov 19;12(22):5270-3. doi: 10.1021/ol1023213. Epub 2010 Oct 29. PMID: 21033728.
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Org Lett. 2010 Nov 19;12(22):5270-3. doi: 10.1021/ol1023213. Epub 2010 Oct 29.

Catalytic enantioselective synthesis of secondary allylic alcohols from terminal alkynes and aldehydes via 1-alkenylboron reagents.

Organic letters

Takashi Shono, Toshiro Harada

Affiliations

  1. Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto, Japan, 606-8585.

PMID: 21033728 DOI: 10.1021/ol1023213

Abstract

A practical one-pot method has been developed for preparing enantioenriched secondary allylic alcohols starting from terminal alkynes and aldehydes. Hydroboration of terminal alkynes with dicyclohexylborane and subsequent reaction of the resulting alkenylboron reagents with aldehydes in the presence of a catalytic amount (5 mol %) of 3-(3,5-diphenylphenyl)-H(8)-BINOL and excess titanium tetraisopropoxide afforded the corresponding allylic alcohols in high enantioselectivities up to 94% ee.

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