SOLVENT-INDUCED ISOMERIZATION OF 2-CYCLOHEXEN-1-OL TO 3-CYCLOHEXEN-1-OL BY A CHIRAL LITHIUM AMIDE

Authors
KHAN AZQ ARVIDSSON PI AHLBERG P
Citation
Azq. Khan et al., SOLVENT-INDUCED ISOMERIZATION OF 2-CYCLOHEXEN-1-OL TO 3-CYCLOHEXEN-1-OL BY A CHIRAL LITHIUM AMIDE, Tetrahedron : asymmetry, 7(2), 1996, pp. 399-402
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
2
Year of publication
1996
Pages
399 - 402
Database
ISI
SICI code
0957-4166(1996)7:2<399:SIO2T3>2.0.ZU;2-L
Abstract
Enantioselective deprotonation by lithium (S)-1-(2-pyrrolidinylmethyl) pyrrolidine 1 of cyclohexene oxide 2 on changing the solvent from tetr ahydrofuran (THF) to cis-2,5-dimethyl-THF (cis-DMTHF) gives the homoal lylic alcohol 3-cyclohexen-1-ol 4 up to 74% yield as isomerized produc t besides the 2-cyclohexen-1-ol 3. In the mixed solvent (THF/cis-DMTHF ) 4 was isolated up to 51% yield (25% ee for (S)-4) and 3 in 42% yield (66% ee for (S)-3). In a separate experiment racemic 3 isomerized to racemic 4 in 74% yield when excess of 1 in DMTHF was used.