Enantioselective 1,4-addition of aryllithium reagents to α,β- unsaturated tert-butyl esters in the presence of chiral additives

Tetrahedron Asymmetry

Volumn 9, Issue 10, 1998, Pages 1651-1655

  Xu, Feng ^a   Tillyer, Richard D ^a   Tschaen, David M ^a   Grabowski, Edward J J ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE; DIAMINE; LITHIUM;

ARTICLE; CHIRALITY; CONFORMATIONAL TRANSITION; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032557499     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00157-8     Document Type: Article

References (20)

1. (a) Mueller, A. L.; Moe, S. T.; Balandrin, M. F.; Delmar, E. G.; Vanwagenen, B. C.; Artman, L. D.; Barmore, R. M.; Smith, D. L. Patent WO 96/40097, June 5, 1995.
2. (b) Johnson, R. E.; Busacca, C. A. Patent US 5,098,901, March 24, 1991.
3. Mannhold, R.; Caldirola, P. L.; Bijloo, G. J.; Timmerman, H. Eur. J. Med. Chem. 1993, 28, 727.
4. (a) Jones, G.; Maisey, R. F.; Somerville, A. R.; Whittle, B. A. J. Med. Chem. 1971, 14, 161.
5. (b) Corey, E. J.; Gant, T. G. Tetrahedron Lett. 1994, 35, 5371.
6. For recent reviews of conjugate addition chemistry see (a) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1992, 92, 771.
7. (b) Perlmutter, P. Conjugated Addition Reactions in Organic Synthesis; Tetrahedron Organic Series; Pergamon Press: Oxford, 1992, Vol. 9.
8. (a) Alexakis, A.; Sedrani, R.; Mangency, P.; Normant, J. F. Tetrahedron Lett. 1988, 29, 4411.
9. (b) Christenson, B.; Hallnemo, G.; Ullenius, C. Tetrahedron 1991, 47, 4739.
10. (c) Malmberg, H.; Nilsson, M.; Ullenius C. Tetrahedron Lett. 1982, 23, 3823.
11. (d) Andersson, S.; Jagner, S.; Nillsson, M.; Urso, F. J. Organomet. Chem. 1986, 301, 257.
12. Frey, L. F.; Tillyer, R. D.; Caille, A.; Tschaen, D. M.; Dolling, U.; Grabowski, E. J. J. J. Org. Chem. 1998, in press.
13. For conjugate addition of organolithium reagents to naphthyl BHA esters and unsaturated imines in the presence of chiral additives see (a) Tomioka, K.; Shindo, M.; Koga, K. Tetrahedron Lett. 1993, 34, 681.
14. (b) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266. For carbolithiation of cinnamyl alcohol derivatives by organolithium reagents mediated by (-)-sparteine see Norsikian S.; Marek, I.; Normant, J. Tetrahedron Lett. 1997, 38, 7523 and associated references.
15. (b) Tomioka, K.; Shindo, M.; Koga, K. J. Am. Chem. Soc. 1989, 111, 8266. For carbolithiation of cinnamyl alcohol derivatives by organolithium reagents mediated by (-)-sparteine see Norsikian S.; Marek, I.; Normant, J. Tetrahedron Lett. 1997, 38, 7523 and associated references.
16. 6Li NMR spectroscopy, showed a singlet due to LiBr-sparteine complex and at least seven signals indicating a complex mixture of species.
17. 2 as modifier).
18. Lithium-bromine exchange of 7 in the presence of (-)-Troger's base 10 required 0.4 equiv. of THF to be added to proceed to completion. It was found that trace amounts of THF rapidly accelerated the lithium halogen exchange reaction in non-polar solvents in the presence or absence of chiral additive.
19. Tomioka has very recently reported the conjugate addition reactions of simple organolithium reagents (MeLi, BuLi, PhLi) to α,β-unsaturated BHA esters mediated by sparteine and diether 9. Asano, Y.; Iida, A; Tomioka, K. Tetrahedron Lett. 1997, 38, 8973.
20. 3, 1.5 equiv. t-butyl acrylate, DMF, 120°C) or direct esterification of the corresponding carboxylic acids with N,N′-diisopropyl-O-tert-butylisourea (Mathias, L. J. Synthesis 1979, 561).