A Novel Highly Effective Chiral Lithium Amide for Catalytic Enantioselective Deprotonation of meso-Epoxides
โ Scribed by Masatoshi Asami; Takashi Suga; Kiyoshi Honda; Seiichi Inoue
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 531 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
A highlyenantioaelectivedeprotonationof meso-epoxideswas achievedby a catalyticamount of a new chiral lithiumamide, derived from (ZS,3aS,7aS)-2-(pyrrolidin-l-ylmethyl)octahydrO indole, in the presenceof excesalithiumdiisopropylamideto afford the correspondingallylic alcoholderivatives up to9470ee. 0 1997 Elsevier ScienceLtd.
๐ SIMILAR VOLUMES
R)-2-Cyclohexen-l-ol and (R)-2-cyclooctene-l-ol have been prepared in very good ee using R,R-homochiral bis-lithium amide bases derived from homochiral C 2 symmetric diamines. (R)-2-Cyclohexen-l-ol has been synthesized in good ee utilising catalytic homochiral bis-lithium amide in the presence of n-
a-Pinene based novel chiral lithium amides have been used for the catalytic enantioselective deprotonation of cyclohexene oxide. An enantiomeric excess of up to 95% for (R)-2-scyclohexen-1-ol was achieved with lithium (-)-N,Ndiisopinocampheylamide. A systematic study shows that the isopinocampheyl m