An experimental and theoretical study of the enantioselective deprotonation of cyclohexene oxide with isopinocampheyl-based chiral lithium amides

Journal of Molecular Modeling

Volumn 12, Issue 5, 2006, Pages 681-686

  Xiao, Ying ^a   Jung, Dawoon ^a   Gund, Tamara ^a   Malhotra, Sanjay V ^a  

^a NEW JERSEY INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

B3LYP 6 31+G(3df,2p); Chiral lithium amides; Cyclohexene oxide; Density functional activation energy; Enantioselective deprotonation; Theoretical study

Indexed keywords

AMIDE; CYCLOHEXANE OXIDE; CYCLOHEXENE DERIVATIVE; LITHIUM DERIVATIVE;

AB INITIO CALCULATION; ARTICLE; CHIRALITY; CONTROLLED STUDY; DATA ANALYSIS; DENSITY FUNCTIONAL THEORY; ENANTIOMER; ENANTIOSELECTIVITY; ENERGY; EXPERIMENTAL STUDY; NORMAL DISTRIBUTION; PRIORITY JOURNAL; PROTON TRANSPORT; QUANTUM CHEMISTRY; THEORETICAL STUDY;

AMIDES; CATALYSIS; CYCLOHEXENES; LITHIUM; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROTONS; STEREOISOMERISM;

EID: 33746421024     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-006-0114-2     Document Type: Article

References (21)

1. Koga K (1995) New Methods Drug Res 4:25-27
2. O'Brien P (1998) J Chem Soc Perkin Trans 1:1439-1457
3. Simpkins NS (1996) Asymmetric deprotonation reactions using enantiopure lithium amide bases. In: Stephenson GR (ed) Advanced asymmetric synthesis. Blackie, Glasgow, Scotland, pp 111-125
4. Thummel RP, Rickborn B (1970) J Am Chem Soc 92:2064-2067
5. Whitesell JK, Felman SW (1980) J Org Chem 45:755-756
6. Simpkins NS (2000) Chimia 54:53-54
7. Cox PJ, Simpkins NS (1991) Tetrahedron: Asymmetry 2:1-26
8. Simpkins NS (1996) Pure Appl Chem 68:691-694
9. Jones S (2002) J Chem Soc Perkin Trans 1:1-21
10. O'Brien P (2001) J Chem Soc Perkin Trans 1:95-113
11. Koga K (1994) Pure Appl Chem 66:1487-1492
12. Brown HC, Kramer GW, Levy AB, Midland MM (1975) Organic synthesis via Boranes. Wiley, New York
13. Brown HC, Ramachandran PV (1996) Sixty years of hydride reductions. In: Abdel-Magid AF (ed) Reductions in organic synthesis. American Chemical Society, Washington, DC, pp 1-30
14. Malhotra SV (2003) Tetrahedron: Asymmetry 14:645-647
15. Asami M (1985) Tetrahedron Lett 26:5803-5806
16. Asami M, Ishizaki T, Inoue S (1994) Tetrahedron: Asymmetry 5:793-796
17. Toukoniitty E, Nieminen V, Taskinen A, Paivarinta J, Hotokka M, Murzin DY (2004) J Catal 224:326-339
18. Brandt P, Hedberg C, Lawonn K, Pinho P, Andersson PG (1999) Chem Eur J 5:1692-1699
19. Foresman JB, Keith TA, Wiberg KB, Snoonian J, Frisch MJ (1996) J Phys Chem 100:16098-16104
20. Sodergren MJ, Andersson PG (1998) J Am Chem Soc 120:10760-10761
21. Gayet A, Bertilsson S, Andersson PG (2002) Org Lett 4:3777-3779