Diastereo- and Enantioselective Synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via Allenylboronate Kinetic Resolution with (dIpc)2BH and Aldehyde Allylboration
2012
Han, Jeng-Liang | Chen, Ming | Roush, William R.
Enantioselective hydroboration of racemic allenylboronate (±)-1 with 0.48 equiv of (ᵈIpc)₂BH at −25 °C proceeds with efficient kinetic resolution and provides allylborane (R)-Z-4. When heated to 95 °C, allylborane (R)-Z-4 isomerizes to the thermodynamically more stable allylborane isomer (S)-E-7. Subsequent allylboration of aldehydes with (R)-Z-4 or (S)-E-7 at −78 °C followed by oxidative workup provides 1,2-syn- or 1,2-anti-diols, 2 or 3, respectively, in 87–94% ee.
显示更多 [+] 显示较少 [-]AGROVOC关键词
书目信息
Organic letters
卷
14
期
12
页码
3028
- 3031
ISSN
1523-7052
出版者
Elsevier B.V.
其它主题
Enantioselective synthesis; Isomers; Enantioselectivity
语言
英语
许可
//data.crossref.org/schemas/AccessIndicators.xsd:license_ref>http://purl.org/eprint/accessRights/OpenAccess | //data.crossref.org/schemas/AccessIndicators.xsd:program>//data.crossref.org/schemas/AccessIndicators.xsd:license_ref> | //data.crossref.org/schemas/AccessIndicators.xsd:program>
类型
Text; Journal Article
2024-02-27
MODS
