期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 136, 期 47, 页码 16515-16521出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja506284w
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资金
- The Funding Program for Next Generation World-Leading Researchers (NEXT Program) [GR002]
- JSPS KAKENHI [26.2447]
- Grants-in-Aid for Scientific Research [14J02447, 26620053] Funding Source: KAKEN
A new method has been developed for the catalytic asymmetric synthesis of alpha-chiral linear or carbocyclic (gamma-alkoxyallyl)boronates via the copper(I)-catalyzed gamma-boryl substitution of allyl acetals. This reaction afforded the products in high yields with excellent E:Z selectivities and enantioselectivities [only (E)-product, 9198% ee] and also exhibited high functional group compatibility. Subsequent allylation of aldehydes with the alpha-chiral (gamma-alkoxyallyl)boronates provided the anti-1,2-diol derivatives in a highly stereospecific manner, and the utility of the alpha-chiral (gamma-alkoxyallyl)boronates was further demonstrated by a convergent coupling of a complex polyol derivative using a (gamma-alkoxyallyl)boronate and a chiral alpha-oxyaldehyde. The stereoselective modular construction of a complex 3,3-disubstituted cyclopentene containing three consecutive stereocenters including a quaternary chiral carbon was also reported. Useful transformations of the alpha-chiral linear (gamma-alkoxyallyl)boronates were also demonstrated.
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