|
|||||
|
|
A DFT exploration of the enantioselective rearrangement of cyclohexene oxide to cyclohexenol |
|
| Authors: | Peter Brandt Per-Ola NorrbyPher G. Andersson |
| Affiliation: | a Department of Structural Chemistry, Biovitrum AB, 112 76 Stockholm, Sweden b Department of Chemistry, Technical University of Denmark, Building 201, Kemitorvet, DK-2800 Kgs Lyngby, Denmark c Department of Organic Chemistry, Institute of Chemistry, Uppsala University, Box 531, S-751 21 Uppsala, Sweden |
| Abstract: | In this paper, we present computational results for the (1S,3R,4R)-3-(pyrrolidinyl)-methyl-2-azabicyclo[2.2.1]heptane mediated rearrangement of cyclohexene oxide. The results nicely explain the differences in enantioselectivities between catalytic and stoichiometric mode between different ligands, and provides a rational for the identification of non-stereospecific background reactions as the major cause of decreased enantioselectivity in catalytic reactions for sterically hindered diamines. |
| Keywords: | α-deprotonation enantioselectivity cyclohexene oxide |
| 本文献已被 ScienceDirect 等数据库收录！ | |