4.8 Article

Construction of Homoallylic Alcohols from Terminal Alkynes and Aldehydes with Installation of syn-Stereochemistry

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 17, Pages 6223-6226

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja502169d

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Funding

  1. MEXT [22105005, 24106718, 23685019, 23350041]
  2. JST (ACT-C)
  3. Grants-in-Aid for Scientific Research [23350041, 22105005, 24106718, 23685019] Funding Source: KAKEN

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A cationic rhodium(I) catalyst turns 2-silyl-1-alkenylboronate, readily prepared from a terminal alkyne, into the corresponding allylboronate species, which immediately undergoes nucleophilic addition to an aldehyde to give a syn-homoallylic alcohol stereoselectively.

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