A new look at boron enolate chemistry: Aminative C-C bond formation using diaminoboron enolate with aldehyde

Organic Letters

Volumn 6, Issue 7, 2004, Pages 1167-1169

  Suginome, Michinori ^a   Uehlin, Lars ^a   Yamamoto, Akihiko ^a   Murakami, Masahiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORON DERIVATIVE; BORON ENOLATE; CARBON; KETONE; UNCLASSIFIED DRUG;

AMINATION; ANALYTIC METHOD; ARTICLE; CHEMICAL BOND; CHEMICAL PROCEDURES; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; STRUCTURE ANALYSIS;

EID: 2342451127     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0497436     Document Type: Article

References (16)

1. Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol 2 p 239.
2. For diastereoselectivity in boron-mediated aldol reactions, see: (a) Masamune, S.; Mori, S.; Van Horn, D.; Brooks, D. W. Tetrahedron Lett. 1979, 20, 1665. (b) Evans, D. A.; Vogel, E.; Nelson, J. V. J. Am. Chem. Soc. 1979, 101, 6120. (c) Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099.
3. For diastereoselectivity in boron-mediated aldol reactions, see: (a) Masamune, S.; Mori, S.; Van Horn, D.; Brooks, D. W. Tetrahedron Lett. 1979, 20, 1665. (b) Evans, D. A.; Vogel, E.; Nelson, J. V. J. Am. Chem. Soc. 1979, 101, 6120. (c) Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099.
4. For diastereoselectivity in boron-mediated aldol reactions, see: (a) Masamune, S.; Mori, S.; Van Horn, D.; Brooks, D. W. Tetrahedron Lett. 1979, 20, 1665. (b) Evans, D. A.; Vogel, E.; Nelson, J. V. J. Am. Chem. Soc. 1979, 101, 6120. (c) Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099.
5. For asymmetric aldol reactions using boron enolates, see: (a) Masamune, S.; Sato, T.; Kim, B.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (b) Paterson, I.; Lister, M. A.; McClure, C. K. Tetrahedron Lett. 1986, 27, 4787. (c) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493. (d) Review: Cowden, C. J.; Paterson, I. Org. React. 1997, 57, 1.
6. For asymmetric aldol reactions using boron enolates, see: (a) Masamune, S.; Sato, T.; Kim, B.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (b) Paterson, I.; Lister, M. A.; McClure, C. K. Tetrahedron Lett. 1986, 27, 4787. (c) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493. (d) Review: Cowden, C. J.; Paterson, I. Org. React. 1997, 57, 1.
7. For asymmetric aldol reactions using boron enolates, see: (a) Masamune, S.; Sato, T.; Kim, B.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (b) Paterson, I.; Lister, M. A.; McClure, C. K. Tetrahedron Lett. 1986, 27, 4787. (c) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493. (d) Review: Cowden, C. J.; Paterson, I. Org. React. 1997, 57, 1.
8. For asymmetric aldol reactions using boron enolates, see: (a) Masamune, S.; Sato, T.; Kim, B.; Wollmann, T. A. J. Am. Chem. Soc. 1986, 108, 8279. (b) Paterson, I.; Lister, M. A.; McClure, C. K. Tetrahedron Lett. 1986, 27, 4787. (c) Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493. (d) Review: Cowden, C. J.; Paterson, I. Org. React. 1997, 57, 1.
9. Suginome, M.; Yamamoto, A.; Ito, Y. Chem. Commun. 2002, 1392.
10. Bernardi, L.; Bonini, B. F.; Capito, E.; Dessole, G.; Fochi, M.; ComesFranchini, M.; Ricci, A. Synlett 2003, 1778.
11. Sugasawa, T.; Toyoda, T. Synth. Commun. 1979, 9, 553.
12. Recent review of the Mannich reaction: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044.
13. Hoffmann, R. W.; Ditrich, K.; Fröch, S. Ann. Chem. 1987, 977.
14. Sugasawa, T.; Toyoda, T.; Sakakura, K. Synth. Commun. 1979, 9, 583.
15. The boron enolates 2a, 2b, 2d, and 2e were prepared from the corresponding lithium enolates with chlorobis(dialkylamino)boranes and used after distillation. The enolate 2c was prepared via amino exchange by reaction of 2a with pyrrolidine (3-4 equiv). The boron enolates generated by the amino exchange reaction were used after evaporation of volatile materials in vacuo.
16. 1H NMR with an internal standard for crude β-amino ketones, which were obtained by acid/base extraction (see Supporting Information). In all cases, a purity >90% was achieved.