Extension to the Silyl-Tethered Radical Cyclization: Cyclohex-2-en-1-oxy Vinyl Silanes in Stereoselective Radical Addition/Cyclization Cascades

Andrey A. Mikhaylov; Samir Z. Zard

doi:10.1021/acs.orglett.7b00627

Extension to the Silyl-Tethered Radical Cyclization: Cyclohex-2-en-1-oxy Vinyl Silanes in Stereoselective Radical Addition/Cyclization Cascades

Andrey A. Mikhaylov, Samir Z. Zard

Laboratoire de Synthèse Organique

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

Abstract

A novel radical cascade reaction of xanthates with 1-[(vinyldimethylsilyl)oxy]cyclohex-2-enes is developed. Due to the steric and electronic differentiation of the two olefinic functions, exclusive regioselectivity and high stereoselectivity of the addition-cyclization are observed. Several methods for modification of both the silicon tether and the xanthate function are reported.

Original language	English
Pages (from-to)	1866-1869
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.7b00627
Publication status	Published - 7 Apr 2017
Externally published	Yes

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10.1021/acs.orglett.7b00627

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title = "Extension to the Silyl-Tethered Radical Cyclization: Cyclohex-2-en-1-oxy Vinyl Silanes in Stereoselective Radical Addition/Cyclization Cascades",

abstract = "A novel radical cascade reaction of xanthates with 1-[(vinyldimethylsilyl)oxy]cyclohex-2-enes is developed. Due to the steric and electronic differentiation of the two olefinic functions, exclusive regioselectivity and high stereoselectivity of the addition-cyclization are observed. Several methods for modification of both the silicon tether and the xanthate function are reported.",

author = "Mikhaylov, \{Andrey A.\} and Zard, \{Samir Z.\}",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

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doi = "10.1021/acs.orglett.7b00627",

language = "English",

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AU - Mikhaylov, Andrey A.

AU - Zard, Samir Z.

PY - 2017/4/7

Y1 - 2017/4/7

N2 - A novel radical cascade reaction of xanthates with 1-[(vinyldimethylsilyl)oxy]cyclohex-2-enes is developed. Due to the steric and electronic differentiation of the two olefinic functions, exclusive regioselectivity and high stereoselectivity of the addition-cyclization are observed. Several methods for modification of both the silicon tether and the xanthate function are reported.

AB - A novel radical cascade reaction of xanthates with 1-[(vinyldimethylsilyl)oxy]cyclohex-2-enes is developed. Due to the steric and electronic differentiation of the two olefinic functions, exclusive regioselectivity and high stereoselectivity of the addition-cyclization are observed. Several methods for modification of both the silicon tether and the xanthate function are reported.

U2 - 10.1021/acs.orglett.7b00627

DO - 10.1021/acs.orglett.7b00627

M3 - Article

C2 - 28358488

AN - SCOPUS:85017141532

SN - 1523-7060

VL - 19

SP - 1866

EP - 1869

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -

Extension to the Silyl-Tethered Radical Cyclization: Cyclohex-2-en-1-oxy Vinyl Silanes in Stereoselective Radical Addition/Cyclization Cascades

Abstract

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