Spin-directed stereoselectivity of carbonyl-alkene photocycloadditions

被引：33

作者：

Griesbeck, AG

Fiege, M

Bondock, S

Gudipati, MS

机构：

[1] Univ Cologne, Inst Organ Chem, D-50939 Cologne, Germany

[2] Univ Cologne, Inst Phys Chem, D-50939 Cologne, Germany

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 23期

关键词：

D O I：

10.1021/ol006502z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The concentration dependence of the Paterno-BUchi photocycloaddition of the two cyclic enolethers 2,3-dihydrofuran and 2,3-dihydropyran, respectively, with aromatic as well as aliphatic aldehydes was studied. For aliphatic aldehydes, a sharp transition from low to high diastereostereoselectivity was observed, indicating a switch from singlet to triplet photocycloaddition with different selectivity controlling mechanisms.

引用

页码：3623 / 3625

页数：3

共 17 条

[1] Paterno-Buchi photocyclization of 2-siloxyfurans and carbonyl compounds.: Notable substituent and carbonyl (aldehyde vs ketone and singlet- vs triplet-excited state) effects on the regioselectivity (double-bond selection) in the formation of bicyclic exo-oxetanes [J].