Regio- and stereoselective acylation of saturated carbocycles via Norrish-Yang photocyclization |
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Authors: | Shin Kamijo |
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Affiliation: | Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan |
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Abstract: | A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish-Yang photocyclization of 1,2-diketones and subsequent ring opening of the α-hydroxy-cyclobutanones. The C-H activation of the carbocycle proceeds regioselectively at vicinal to the diketone moiety resulting in stereoselective formation of cis-fused bicycles. The following C-C cleavage affords vicinally cis-acylated carbocycles. Predictability, generality, and practicality of the present strategy have been demonstrated using variously modified saturated carbocycles. |
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