Regio- and stereoselective acylation of saturated carbocycles via Norrish–Yang photocyclization
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 vic...
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Published in | Tetrahedron letters Vol. 51; no. 5; pp. 872 - 874 |
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Main Authors | , , |
Format | Journal Article |
Language | English |
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03.02.2010
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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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AbstractList | 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 alpha-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. (C) 2009 Elsevier Ltd. All rights reserved. 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. |
Author | Inoue, Masayuki Kamijo, Shin Hoshikawa, Tamaki |
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Keywords | FUNCTIONALIZATION STEREOCONTROLLED PHOTOCYCLIZATION KETONES 1,2-DIKETONES ADAMANTANES PHOTOCHEMICAL-REACTIONS ALKANES |
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Snippet | A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish–Yang photocyclization of... A regio- and stereoselective acylation of saturated carbocycles has been achieved through two-step reactions involving the Norrish-Yang photocyclization of... |
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SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
Title | Regio- and stereoselective acylation of saturated carbocycles via Norrish–Yang photocyclization |
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