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-
Preparation of proline derived lithium amide bases and their use in enantioselective deprotonation of meso epoxides
โ Scribed by Shirley K. Hendrie; John Leonard
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 443 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4020
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โฆ Synopsis
oMo-4ozo/87 53.00+.00 Q 1987 Perpmon loumals Ltd. s. K. HENDRIB and J. b3NARD Ownlw Of t~8a~utyl~lmothy~~~,~x~clopmtme 15 to Inn~tbutyldlmothylsllox~2. cycl0pmtsn-bd 17. nBuVl lwlhrm (O.!Xml, 1 .5M, O.Ummol) wa6 adrIed to a 8ok@n of (S)-2-R Wrro-U48mg, 0.~1. h dryether(3cnr3)etOoC,under~.Aflsr30~.Me~epoxide(100mg,054mnol),hsWer(2an3)~addedandthe~n, wasa!iowedtowarmtomomt ~andsthedwlynoepoxlde~,asindcatedbync~abM8hr.~.Thes0clhbn~ then diluted with CH$b, washed with water, d&d, ev~rated and the resldur puryled hy l&h dwomatogrephy.
'I+ NMR (60 MHz) 6 0.0 (6, SJ-I), 0.8 (s. 9H), 2.6 (m, 2H), 4.9 (m, ZH), 5.8 (s, 2li);v, 3350,%%0,1060, cm-l.
๐ SIMILAR VOLUMES
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