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Formal [4+3] epoxide cascade reaction via a complementary ambiphilic pairing strategy.

ABSTRACT: A formal [4+3] epoxide cascade protocol utilizing ambiphilic sulfonamides and a variety of epoxides (masked ambiphiles) has been developed for the generation of benzothiaoxazepine-1,1'-dioxides and oxathiazepine-1,1'-dioxides. This protocol combines an epoxide ring-opening with either an S(N)Ar or oxa-Michael cyclization pathway.

SUBMITTER: Rolfe A 

PROVIDER: S-EPMC2864497 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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Formal [4+3] epoxide cascade reaction via a complementary ambiphilic pairing strategy.

Rolfe Alan A   Samarakoon Thiwanka B TB   Hanson Paul R PR  

Organic letters 20100301 6

A formal [4+3] epoxide cascade protocol utilizing ambiphilic sulfonamides and a variety of epoxides (masked ambiphiles) has been developed for the generation of benzothiaoxazepine-1,1'-dioxides and oxathiazepine-1,1'-dioxides. This protocol combines an epoxide ring-opening with either an S(N)Ar or oxa-Michael cyclization pathway. ...[more]

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