Catalytic, enantioselective, intramolecular carbosulfenylation of olefins. Preparative and stereochemical aspects.
Catalytic, enantioselective, intramolecular carbosulfenylation of olefins. Preparative and stereochemical aspects.
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DOI：
10.1021/jo4023765
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发表时间：
2014-01-03
期刊：
影响因子：
--
通讯作者：
Jaunet A
中科院分区：
文献类型：
--
作者：
Denmark SE;Jaunet A
The first catalytic, enantioselective, intramolecular carbosulfenylation of isolated alkenes with aromatic nucleophiles is described. The combination of N-phenylsulfenylphthalimide, a chiral selenophosphoramide derived from BINAM, and ethanesulfonic acid as a co-catalytic Brønsted acid induced an efficient and selective cyclofunctionalization of various alkenes (aliphatic and aromatic) tethered to a 3,4-methylenedioxyphenyl ring. Under these conditions, 6-phenylthio-5,6,7,8-tetrahydronaphthalenes are formed diastereospecifically in good yields (50–92%) and high enantioselectivities (71:29 – 97:3 er). E-Alkenes reacted much more rapidly and with much higher selectivity than Z-alkenes, whereas electron rich alkenes reacted more rapidly but with comparable selectivity to electron-neutral alkenes and electron deficient alkenes. The Brønsted acid played a critical role in effecting reproducible enantioselectivity. A model for the origin of enantioselectivity and the dependence of rate and selectivity on alkene structure is proposed along with a rationale for the site selectivity in reactions with mono-activated arene nucleophiles.
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DOI：
10.1039/p19830000751
发表时间：
1983-01-01
期刊：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
影响因子：
--
作者：
AMUPITAN, JA;HUQ, E;SUTHERLAND, JK
通讯作者：
SUTHERLAND, JK
影响因子：
6.7
作者：
BROWN, TH;BLAKEMORE, RC;WALKER, TF
通讯作者：
WALKER, TF
未保护的 3-取代羟吲哚的催化不对称磺酰化
影响因子：
5.2
作者：
Cai, Yunfei;Li, Jun;Feng, Xiaoming
通讯作者：
Feng, Xiaoming
影响因子：
15
作者：
Denmark, Scott E.;Collins, William R.;Cullen, Matthew D.
通讯作者：
Cullen, Matthew D.
影响因子：
15
作者：
Denmark, Scott E.;Kornfilt, David J. P.;Vogler, Thomas
通讯作者：
Vogler, Thomas