Asymmetric induction in intramolecular [2+ 2]-photocycloadditions of 1, 3-disubstituted allenes with enones and enoates

EM Carreira, CA Hastings, MS Shepard…

Index: Carreira, Erick M.; Hastings, Curtis A.; Shepard, Mary S.; Yerkey, Lori A.; Millward, Dan B. Journal of the American Chemical Society, 1994 , vol. 116, # 15 p. 6622 - 6630

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Citation Number: 34

Abstract

Abstract: Irradiation of optically active allenes (89-92% ee) appended to enones and enoates affords alkylidenecyclobutane photoadducts with high levels of asymmetric induction (83-1004) derived exclusively from the allene fragment. The substrates studied include allenes tethered to enones such as 1, 3-~ yclohexanedione and 1, 3-~ yclopentanedione, as well as allenes tethered to functionalized coumarins. The ...

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