TY - JOUR
T1 - Stereoselective access to highly substituted vinyl ethers via trans-difunctionalization of alkynes with alcohols and iodine(iii) electrophile
AU - Ding, Wei
AU - Chai, Jinkui
AU - Wang, Chen
AU - Wu, Junliang
AU - Yoshikai, Naohiko
N1 - Funding Information:
This work was supported by the Ministry of Education (Singapore) and Nanyang Technological University (MOE2016-T2-2-043 and RG114/18). We thank Dr. Yongxin Li (Nanyang Technological University) for his assistance with the X-ray crystallographic analysis.
Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/5/13
Y1 - 2020/5/13
N2 - A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as various alcohols, affording β-λ3-iodanyl vinyl ethers in good yields with high regio- and stereoselectivities. The benziodoxole moiety of the products can be used as a versatile linchpin for the synthesis of structurally diverse vinyl ethers that are difficult to access by other means.
AB - A method for the regio- and stereoselective synthesis of highly substituted vinyl ethers via trans-1,2-difunctionalization of alkynes with a cyclic λ3-iodane electrophile (benziodoxole triflate) and alcohols is reported. The reaction tolerates a variety of internal and terminal alkynes as well as various alcohols, affording β-λ3-iodanyl vinyl ethers in good yields with high regio- and stereoselectivities. The benziodoxole moiety of the products can be used as a versatile linchpin for the synthesis of structurally diverse vinyl ethers that are difficult to access by other means.
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U2 - 10.1021/jacs.0c04140
DO - 10.1021/jacs.0c04140
M3 - Article
C2 - 32362119
AN - SCOPUS:85085695991
VL - 142
SP - 8619
EP - 8624
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 19
ER -