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...

Full description

Saved in:
Bibliographic Details
Published inTetrahedron letters Vol. 51; no. 5; pp. 872 - 874
Main Authors Kamijo, Shin, Hoshikawa, Tamaki, Inoue, Masayuki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.02.2010
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FUNCTIONALIZATION
STEREOCONTROLLED PHOTOCYCLIZATION
KETONES
1,2-DIKETONES
ADAMANTANES
PHOTOCHEMICAL-REACTIONS
ALKANES
Online AccessGet full text

Cover

More Information
Summary: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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.12.027