Highly efficient binary and remote asymmetric induction from a single allyltin reagent with a chiral carbamate moiety

Synlett

Volumn , Issue 16, 2005, Pages 2519-2521

  Nishigaichi, Yutaka ^a   Ueda, Narifumi ^a   Tamura, Ken Ichi ^a   Takuwa, Akio ^a  

^a SHIMANE UNIVERSITY   (Japan)

Author keywords

Allylations; Lewis acids; Protecting groups; Stereoselective synthesis; Tin

Indexed keywords

ALDEHYDE DERIVATIVE; CARBAMIC ACID DERIVATIVE; LEWIS ACID;

ALLYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOCHEMISTRY;

EID: 26844523257     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-917081     Document Type: Article

References (21)

1. Diastereoselection, Gung, B. W.; le Noble, B., Eds.; Chem. Rev. 1999, 99, 1067-1480.
2. (a) Mikami, K.; Shimizu, M.; Zhang, H.-C.; Maryanoff, B. E. Tetrahedron 2001, 57, 2917.
3. (b) Denmark, S. E.; Fu, J. Chem. Rev. 2003, 103, 2763; see also the references cited therein.
4. Nishigaichi, Y.; Kuramoto, H.; Takuwa, A. Tetrahedron Lett. 1995, 36, 3353.
5. Thomas group and Dias group also reported similar asymmetric induction. See: (a) Almendros, P.; Gruttadauria, M.; Helliwell, M.; Thomas, E. J. J. Chem. Soc., Perkin Trans. 1 1997, 2549.
6. (b) Dias, L. C.; Steil, L. J. Tetrahedron Lett. 2004, 45, 8835; see also the references cited therein.
7. (a) Maguire, R. J.; Mulzer, J.; Bats, W. J. Org. Chem. 1996, 61, 6936.
8. (b) Paquette, L. A.; Bennett, G. D.; Chatriwalla, A.; Isaac, M. B. J. Org. Chem. 1997, 62, 3370.
9. Nishigaichi, Y.; Takuwa, A.; Naruta, Y.; Maruyama, K. Tetrahedron 1993, 49, 7395.
10. Both reagents 2c and 2d were prepared readily from the corresponding alcoholic reagent and methyl chloroformate or dimethylcarbamoyl chloride, respectively.
11. 4. The condensed mixture was purified on silica gel TLC to isolate the products.
12. (a) Stereochemistry of the products was determined by the derivatization and by the comparison with the previously reported compounds. See ref. 3-5. Also refer to: Nishigaichi, Y.; Takuwa, A.; Jodai, A. Tetrahedron Lett. 1991, 32, 2383.
13. 5): 1.38 (d, 3 H, J = 6.6 Hz), 2.42 (dd, 1 H, J = 13.8, 9.3 Hz), 2.50 (dd, 1 H, J = 13.8, 4.8 Hz), 2.93 (s, 3 H), 2.97 (s, 3 H), 3.67 (d, 1 H, J = 3.2 Hz), 4.96 (br s, 1 H), 5.02 (ddd, 1 H, J = 9.3, 4.8, 3.2 Hz), 5.13 (br s, 1 H), 5.16 (q, 1 H, J = 6.6 Hz), 7.36 (m, 5 H).
14. Nishigaichi, Y.; Fujimoto, M.; Nakayama, K.; Takuwa, A.; Hamada, K.; Fujiwara, T. Chem. Lett. 1992, 2339.
15. 2O gave a diastereoisomeric mixture of synlanti = 4:6, which means the transmetallation promoted the preferential formation of the anti-isomer.
16. 4-mediated reaction in ref. 8.
17. Nishigaichi, Y.; Yoshikawa, M.; Takigawa, Y.; Takuwa, A. Chem. Lett. 1996, 961.
18. 2O four times and the combined extracts were washed with brine, dried and condensed. The residue was purified on silica gel TLC.
19. (a) Ashby, E. C.; Prather, J. J. Am. Chem. Soc. 1965, 88, 729.
20. (b) Fieser, L. F.; Fieser, M. Reagents for Organic Synthesis, Vol. 1; John Wiley & Sons: New York, 1967, 595.
21. Recently, Markó group reported a successful application of the carbamate protection to the allylmetal chemistry. See: Dubost, C.; Leroy, B.; Markó, I. E.; Tinant, B.; Declercq, J.-P.; Bryans, J. Tetrahedron 2004, 60, 7693.