An asymmetric cyanation reaction and sequential asymmetric cyanation-nitroaldol reaction using a [YLi3{tris(binaphthoxide)}] single catalyst component: Catalyst tuning with achiral additives

Angewandte Chemie - International Edition

Volumn 41, Issue 19, 2002, Pages 3636-3638

  Tian, Jun ^a   Yamagiwa, Noriyuki ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Asymmetric catalysis; Asymmetric synthesis; Cyanation; Multicomponent reactions; Yttrium

Indexed keywords

ADDITIVES; CATALYSIS; SUBSTRATES;

CYANATION REACTION;

CATALYSTS;

CYANIC ACID; LITHIUM DERIVATIVE; YTTRIUM;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOSELECTIVITY; REACTION ANALYSIS; REACTION OPTIMIZATION;

EID: 0037020417     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021004)41:19<3636::AID-ANIE3636>3.0.CO;2-B     Document Type: Article

References (21)

1. Comprehensive Asymmetric Catalysis (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Heidelberg, 1999.
2. S. Yamasaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 1256, and references therein.
3. a) J. Louie, C. W. Bielawski, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 11312, and references therein;
4. b) P. A. Evans, J. E. Robinson, J. Am. Chem. Soc. 2001, 123, 4609.
5. H.-B. Yu, Q.-S. Hu, L. Pu, J. Am. Chem. Soc. 2000. 122, 6500.
6. 3] and its structural elucidation:
7. 3] and its structural elucidation:
8. b) H. C. Aspinall, J. L. M. Dwyer, N. Greeves, A. Steiner, Organometallics 1999, 18, 1366.
9. Review for additive effects in asymmetric catalysis, see: E. M. Vogl, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 1685; Angew. Chem. Int. Ed. 1999, 38, 1570.
10. Review for additive effects in asymmetric catalysis, see: E. M. Vogl, H. Gröger, M. Shibasaki, Angew. Chem. 1999, 111, 1685; Angew. Chem. Int. Ed. 1999, 38, 1570.
11. For representative examples of catalyst tuning by achiral additives enabling the synthesis of both product enantiomers from one chiral catalyst, see: a) S. Kobayashi, H. Ishitani, J. Am. Chem. Soc. 1994, 116, 4083; b) A. M. Costa, C. Jimeno, J. Gavenonis, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc. 2002, 124, 6929, and references therein.
12. For representative examples of catalyst tuning by achiral additives enabling the synthesis of both product enantiomers from one chiral catalyst, see: a) S. Kobayashi, H. Ishitani, J. Am. Chem. Soc. 1994, 116, 4083; b) A. M. Costa, C. Jimeno, J. Gavenonis, P. J. Carroll, P. J. Walsh, J. Am. Chem. Soc. 2002, 124, 6929, and references therein.
13. a) S. Matsubara, H. Onishi, K. Utimoto, Tetrahedron Lett. 1990, 31, 6209;
14. b) S. E. Schaus, E. N. Jacobsen, Org. Lett. 2000, 2, 1001;
15. c) K. Yabu, S. Masumoto, S. Yamasaki, Y. Hamashima, M. Kanai, W. Du, D. P. Curran, M. Shibasaki, J. Am. Chem. Soc. 2001, 123, 9908.
16. Catalytic asymmetric cyanation of ketones using 3 as a CN source: S.-K. Tian, L. Deng, J. Am. Chem. Soc. 2001, 123, 6195.
17. Other heterobimetallic LnMB complexes (Ln = La, Sm, Gd etc. M = Li, Na, and K) gave less satisfactory results even with additives 5a and/or 5b (<80% ee).
18. a) R. J. H. Gregory, Chem. Rev. 1999, 99, 3649;
19. b) H. Gröger, Chem. Eur. J. 2001, 7, 5246, and references therein.
20. Nitroaldol reactions of benzaldehyde (2a) catalyzed by LnMB (Figure 1) generally afford 7a only in modest ee values: LLB (Ln = La, M = Li) 37% ee, EuLB (Ln = Eu, M = Li) 72% ee (best result among species of general formula LnMB). Thus, the result with 1 (62% ee, Table 3, entry 1) is relatively good among LnMB complexes. See ref. [5a].
21. 2O would be consumed by the reaction with 3.