A new and direct asymmetric synthesis of a hindered chiral amine via a novel sulfinate ketimine derived from N-tosyl-1,2,3-oxathiazolidme-2-oxide: Practical asymmetric synthesis of (R)-sibutramine

Organic Process Research and Development

Volumn 10, Issue 2, 2006, Pages 327-333

  Han, Zhengxu ^a,b   Krishnamurthy, Dhileepkumar ^a,b   Senanayake, Chris H ^a,b  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

^b BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33645539260     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op050182n     Document Type: Article

References (21)

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14. (b) See Experimental Section for details on recovery of the auxiliary.
15. (c) Han, Z.; Krishnamurthy, D.; Grover, P.; Wilkinson, H. C.; Fang, Q. K.; Su, X.; Lu, Z.; Magiera, D.; Senanayake, C. H. Angew. Chem., Int. Ed. 2003, 42, 2032.
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18. See ref 2 for the determination of the stereochemistry of 5.
19. The Experimental Section gives the detail for the preparations of amino alcohols and oxathiazolidines. The absolute stereochemistry of 13e was unambiguously established by single-crystal X-ray analysis.
20. 1H NMR analysis.
21. See Experimental Section for the one-pot procedure for the preparation 5 from 1 and 13e.