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

Résultats de recherche: Contribution à un journal › Article › Revue par des pairs

5 Citations (Scopus)

Résumé

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.

langue originale	Anglais
Pages (de - à)	1866-1869
Nombre de pages	4
journal	Organic Letters
Volume	19
Numéro de publication	7
Les DOIs	https://doi.org/10.1021/acs.orglett.7b00627
état	Publié - 7 avr. 2017
Modification externe	Oui

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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.",

year = "2017",

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

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journal = "Organic Letters",

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T2 - Cyclohex-2-en-1-oxy Vinyl Silanes in Stereoselective Radical Addition/Cyclization Cascades

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

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