Enantioselective construction of quaternary carbon centers by catalytic [2 + 2 + 2] cycloaddition of 1,6-enynes and alkynes

Takanori Shibata; Yoshikazu Arai; Yu Ki Tahara

doi:10.1021/ol051876j

Enantioselective construction of quaternary carbon centers by catalytic [2 + 2 + 2] cycloaddition of 1,6-enynes and alkynes

Takanori Shibata^*, Yoshikazu Arai, Yu Ki Tahara

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

63 Citations (Scopus)

Abstract

(Chemical Equation Presented) The enantioselective [2 + 2 + 2] cycloaddition of 1,6-enynes and alkynes using chiral rhodium catalysts gave cycloadducts containing quaternary carbon stereocenters. Both symmetrical and unsymmetrical alkynes and acetylene could be used as coupling partners, and the corresponding bicyclic cyclohexa-1,3-dienes were obtained in good to excellent ee.

Original language	English
Pages (from-to)	4955-4957
Number of pages	3
Journal	Organic Letters
Volume	7
Issue number	22
DOIs	https://doi.org/10.1021/ol051876j
Publication status	Published - 2005 Oct 27

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol051876j

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abstract = "(Chemical Equation Presented) The enantioselective [2 + 2 + 2] cycloaddition of 1,6-enynes and alkynes using chiral rhodium catalysts gave cycloadducts containing quaternary carbon stereocenters. Both symmetrical and unsymmetrical alkynes and acetylene could be used as coupling partners, and the corresponding bicyclic cyclohexa-1,3-dienes were obtained in good to excellent ee.",

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year = "2005",

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T1 - Enantioselective construction of quaternary carbon centers by catalytic [2 + 2 + 2] cycloaddition of 1,6-enynes and alkynes

AU - Shibata, Takanori

AU - Arai, Yoshikazu

AU - Tahara, Yu Ki

PY - 2005/10/27

Y1 - 2005/10/27

N2 - (Chemical Equation Presented) The enantioselective [2 + 2 + 2] cycloaddition of 1,6-enynes and alkynes using chiral rhodium catalysts gave cycloadducts containing quaternary carbon stereocenters. Both symmetrical and unsymmetrical alkynes and acetylene could be used as coupling partners, and the corresponding bicyclic cyclohexa-1,3-dienes were obtained in good to excellent ee.

AB - (Chemical Equation Presented) The enantioselective [2 + 2 + 2] cycloaddition of 1,6-enynes and alkynes using chiral rhodium catalysts gave cycloadducts containing quaternary carbon stereocenters. Both symmetrical and unsymmetrical alkynes and acetylene could be used as coupling partners, and the corresponding bicyclic cyclohexa-1,3-dienes were obtained in good to excellent ee.

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Enantioselective construction of quaternary carbon centers by catalytic [2 + 2 + 2] cycloaddition of 1,6-enynes and alkynes

Abstract

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