Catalytic asymmetric aminolysis of 3,5,8-trioxabicyclo[5.1.0]octane Providing an optically pure 2-amino-1,3,4-butanetriol equivalent

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4962-4965

  Sagawa, Shoichi ^a   Abe, Hiroyuki ^a   Hase, Yasunori ^a   Inaba, Takashi ^a  

^a JAPAN TOBACCO INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1,3,4 BUTANETRIOL; BENZYLAMINE DERIVATIVE; BUTANE; OCTANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; OPTICAL ROTATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0033603374     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9900883     Document Type: Article

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22. The importance of water in the Lewis acid promoted reaction was previously reported, see: Pitchen, P.; Dunach, E.; Deshmukh, M. N.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 8188. When 1c was subjected to the similar conditions of entry 3 in Table 1 with exclusion of water (0.01 mol %, Karl Fischer), the conversion of the reaction and ee of product 2c were 84% and 46%, respectively.
23. Using an aprotic solvent was crucial to prevent the noncatalyzed reaction. No reaction was observed when the epoxides (1a, 1c, and 5) were treated with the amines (benzylamine and 6) in the absence of the catalyst in toluene or heptane.
24. 4 complex. The methoxyl groups were omitted for clarity in Figure 1.
25. The RMS distance between the heavy atoms of 1c and 1c in 1c+Ti was 0.26 Å.
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29. To avoid the problems related to the preferential hydrogenation of some diastereomer, the completion of the reaction was confirmed by TLC.
30. The ABTE, 8, was used for the practical synthesis of nelfinavir, a potent HIV protease inhibitor, see ref 16.
31. (a) The compound 9, (5R,6S)-6-benzyloxycarbonylamino-2,2-dimethyl-5-hydroxy-1,3-dioxepan, was obtained by treatment of 8 with Cbz-Cl. See the Supporting Information.
32. (b) 2c, 7a, 7b, and 7d were converted into 8 using the similar conditions described in the preparation of 8 from the mixture of 7c and 7d.