Asymmetric α-substitution versus aza Diels–Alder reaction of electron deficient N-sulfonyl imines

PE Morgan, R McCague, A Whiting

Index: Morgan, Paul E.; McCague, Ray; Whiting, Andrew Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 4 p. 515 - 525

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Abstract

Several N-arylsulfonylglycine esters have been brominated under photolytic conditions to provide the corresponding α-bromoglycine. These bromo esters can be treated with a range of bases to generate N-sulfonyl imino esters in situ; attempts to isolate the imines in a pure state were universally unsuccessful. Once generated, the imines can be trapped with cyclopentadiene to provide the corresponding aza Diels–Alder adducts in varying yields, ...