Tetrahedron Asymmetry p. 399 - 402 (1996)
Update date:2022-08-04
Topics:
Khan, Agha Zul-Qarnian
Arvidsson, Per I.
Ahlberg, Per
Enantioselective deprotonation by lithium (S)-1-(2-pyrrolidinylmethyl)pyrrolidine 1 of cyclohexene oxide 2 on changing the solvent from tetrahydrofuran (THF) to cis-2,5-dimethyl-THF (cis-DMTHF) gives the homoallylic alcohol 3-cyclohexen-1-ol 4 up to 74% yield as isomerized product 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.
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