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

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

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 method...

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Veröffentlicht in:Organic letters 2017-04, Vol.19 (7), p.1866-1869
Hauptverfasser: Mikhaylov, Andrey A, Zard, Samir Z
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
Organic chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b00627