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...
Saved in:
Published in | Tetrahedron letters Vol. 51; no. 5; pp. 872 - 874 |
---|---|
Main Authors | , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
03.02.2010
Elsevier |
Subjects | |
Online Access | Get full text |
Cover
Loading…
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 |