The first tandem inter-intramolecular catalytic asymmetric nitroaldol reaction utilizing a LnLi3tris((R)-binaphthoxide) complex ((R)-LnLB) (Ln: Lanthanoid)

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 6031-6034

  Sasai, Hiroaki ^a   Hiroi, Manami ^a   Yamada, Yoichi M A ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDANONE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0030788730     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01341-5     Document Type: Article

References (43)

1. Dedicated to Professor D. Seebach on the occasion of his 60th birthday.
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10. Recent examples of tandem catalytic asymmetric reactions: i) Ohshima, T.; Kagechika, K.; Adachi, M.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc. 1996, 118, 7108.
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23. i)Arai, T.; Yamada, Y. M. A.; Yamamoto, N.; Sasai, H.; Shibasaki, M. Chem. Eur. J. 1996, 2, 1368.
24. j) Sasai, H.; Watanabe, S.; Shibasaki, M. Enantiomer 1997, 2, 267.
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26. 1 was easily synthesized from 2-methyl-1,3-cyclopentanedione and acrolein in one step (89%). See: Schick, H.; Roatsch, B.; Schwarz, H.; Hauser, A.; Schwarz, S. Liebigs Ann. Chem. 1992, 419.
27. A relative configuration of 3a was tentatively assigned as shown in Table 1.
28. 3, Z=4, absorption coefficient = 0.949/mm, F(000) = 488, crystal size = 0.3 × 0.3 × 0.2 mm, θ range for data collection 4.87 to 65.00 deg., index range 0 ≤ h ≤ 12, 0 ≤ K ≤ 19, 0 ≤ l ≤ 7, reflections collected 1112, independent correction 1112 [R (int) = 0.0000], Final R indices [I > 2∑ (I)] R1 = 0.0297 wR2 = 0.0776, R indices (all data) R1 = 0.0308 wR2 = 0.0785 Equation Presented
29. Enantiomeric excess of 3b was determined by chiral HPLC analysis (DAICEL CHIRALPAK AD, flowing eluent hexane/2-propanol (12/1), detected at 230 nm).
30. 2O (22% ee). For LSB, see reference 13a; for ALB, see reference 2k; for LPB, see Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656.; for GaLB, see Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M.; J. Am. Chem. Soc. 1997, 119, 4783.
31. 2O (22% ee). For LSB, see reference 13a; for ALB, see reference 2k; for LPB, see Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656.; for GaLB, see Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M.; J. Am. Chem. Soc. 1997, 119, 4783.
32. The reason for this appears to be that the equilibrium in the intermolecular reactions exists at 50 °C.
33. The reason for this is not clear at present.
34. 3tris((R)-bis((trimethysilyl)ethynyl)binaphthoxide) slightly improved the ee of 3b, the yield of 3b was decreased and an unknown-byproduct was detected. See references 3h, 3i, 3k.
35. 3OH) (96% ee).
36. a) Sasai, H.; Arai, T.; Satow, K.; Houk, K. N.; Shibasaki, M. J. Am. Chem. Soc. 1995, 117, 6194.
37. b) Yamada, Y. M. A.; Yoshikawa, N.; Sasai. H; Shibasaki, M. Angew. Chem. Int. Ed. Engl. 1997, 36, in press.
38. PM3 calculation shows 3b was 1.58 kcal/mol more stable than 3a. For PM3, see Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209.
39. We have already found that there is no equilibrium in an intermolecular nitroaldol reaction catalyzed by LnLB. See reference 3h.
40. Treatment of LLB (3.3 mol %) with 30 mol equiv of nitromethane for 2 days at room temperature prior to use as a catalyst caused a decline in the optical purity of the nitroaldol adduct (19 h, -40 °C; 19% ee, 53% yield, Sasai; H., Tokunaga, T.; Shibasaki, M., unpublished result) generated from hydrocinnamaldehyde and nitromethane (cf. usual method: 60% ee, 88% yield). These results do not necessarily deny the possibility that at room temperature LLB partially decomposes by an interaction with nitromethane to form catalysts with less potential to produce optically active nitroaldol adducts in intramolecular reactions.
41. a) Stork, G.; West, F.; Lee, H.-Y.; Isaacs, R. C. A.; Manabe, S. J. Am. Chem. Soc. 1996, 118, 10660 and references cited therein.
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43. c)Sato, S.; Nakada, M.; Shibasaki, M. Tetrahedron Lett. 1996, 37,6141 and references cited therein.