Synthesis of enantiopure aminocyclopropanes by diastereoselective addition of a chiral amino substituted organozinc carbenoid to alkenes

Synthesis

Volumn , Issue 19, 2005, Pages 3186-3188

  Bégis, Guillaume ^a   Sheppard, Tom D ^a   Cladingboel, David E ^b   Motherwell, William B ^a   Tocher, Derek A ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Alkenes; Carbenoids; Chiral auxiliaries; Electrophilic addition; Zinc

Indexed keywords

SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); ZINC;

CARBENOIDS; CHIRAL AUXILIARIES; ELECTROPHILIC ADDITION;

ORGANIC COMPOUNDS;

ALKENE DERIVATIVE; BELACTOSIN A; CARBENOID; CYCLOPROPANE DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHIRALITY; CYCLOPROPANATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOMER; METHODOLOGY; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 29044443217     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918469     Document Type: Article

References (20)

1. For examples see: (a) Salaün, J. Top. Curr. Chem. 2000, 207, 1.
2. (b) Salaün, J.; Baird, M. S. Curr. Med. Chem. 1995, 2, 511.
3. (a) Aggarwal, V. K.; de Vicente, J.; Bonnert, R. V. Org. Lett. 2001, 3, 2785.
4. (b) de Meijere, A.; Kozhushkov, S. I.; Savchenko, A. I. J. Organomet. Chem. 2004, 689, 2033.
5. Ye, A.; Komarov, I. V.; Kirby, A. J.; Jones, M. J. Jr. J. Org. Chem. 2002, 67, 9288.
6. Lavallo, V.; Mafhouz, J.; Canac, Y.; Donnadieu, B.; Schoeller, W. W.; Bertrand, G. J. Am. Chem. Soc. 2004, 126, 8670.
7. (e) Ogawa, A.; Takami, N.; Nanke, T.; Ohya, S.; Hirao, T. Tetrahedron 1997, 53, 12895.
8. Bégis, G.; Cladingboel, D.; Motherwell, W. B. Chem. Commun. 2003, 2656.
9. Es-Sayed, M.; Gratkowski, C.; Krass, N.; Meyers, A. I.; de Meijere, A. Synlett 1992, 962.
10. Akiba, T.; Tamura, O.; Terashima, S. In Org. Synth. Coll. Vol. X; Wiley: New York, 2004, 374.
11. Gmeimer, P.; Bollinger, B. Synthesis 1995, 168.
12. CCDC Nos. 282755 and 282756 contain the crystallographic data for 14 and 16. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
13. (a) Magar, S. S.; Desai, S. C.; Fuchs, P. L. J. Org. Chem. 1992, 57, 5360.
14. (b) Rahman, N. A.; Fleming, I. Synth. Commun. 1993, 23, 1583.
15. (a) Asai, A.; Hasegawa, A.; Ochiai, K.; Yamashita, Y.; Mizukami, T. J. Antibiotics 2000, 53, 81.
16. (b) Armstrong, A.; Scutt, J. N. Chem. Commun. 2004, 510.
17. Lygo, B.; Andrews, B. I. Acc. Chem.Res. 2004, 37, 518; and references therein.
18. The enantiomeric excess of alkene 21 was > 97% by chiral HPLC after a single recrystallisation.
19. 1H NMR coupling constants.
20. 3 can cause partial degradation to the N-formyl derivative.