STEREOSELECTIVE SYNTHESIS OF TETRAHYDROFURANS AND TETRAHYDROPYRANS BYNI(0) PROMOTED TANDEM CYCLIZATION-CARBONYLATION

Authors
DELGADO A LLEBARIA A CAMPS F MORETO JM
Citation
A. Delgado et al., STEREOSELECTIVE SYNTHESIS OF TETRAHYDROFURANS AND TETRAHYDROPYRANS BYNI(0) PROMOTED TANDEM CYCLIZATION-CARBONYLATION, Tetrahedron letters, 35(23), 1994, pp. 4011-4014
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
23
Year of publication
1994
Pages
4011 - 4014
Database
ISI
SICI code
0040-4039(1994)35:23<4011:SSOTAT>2.0.ZU;2-Q
Abstract
Reaction of different vinyl bromides (1a-3a), beating phenyl substitut ed alkenyloxyalkyl groups, with Ni(CO)4 affords the corresponding subs tituted cyclic ethers 1b-3b in moderate to good yields and high diaste reoselectivity. In the cyclization of 1a, the stereoselectivity of the process can be reversed by the use of additives, such as KOAc, TIOAc, Cs2CO3, and KOCOCF3.