Lewis acid mediated SN2-type nucleophilic ring opening followed by [4+2] cycloaddition of N-tosylazetidines with aldehydes and ketones: synthesis of chiral 1,3-oxazinanes and 1,3-amino alcohols

Tetrahedron Letters

Volumn 48, Issue 25, 2007, Pages 4373-4377

  Ghorai, Manas K ^a   Das, Kalpataru ^a   Kumar, Amit ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

1,3 Amino alcohol; 1,3 Oxazinane; 4+2 Cycloaddition; Carbonyl; Cu(OTf)2; Lewis acid; Mechanism; N Tosylazetidine; Non racemic; Nucleophilic; Ring opening; SN2

Indexed keywords

1,3 AMINO ALCOHOL DERIVATIVE; 1,3 OXAZINANE DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; AZETIDINE DERIVATIVE; LEWIS ACID; N TOSYLAZETIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTAL STRUCTURE; CYCLOADDITION; SYNTHESIS;

EID: 34248683615     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.097     Document Type: Article

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40. Ghorai, M. K.; Kumar, A.; Das, K., unpublished results.
41. 4. The crude product was purified by flash column chromatography on silica gel (230-400 mesh) using 5% ethyl acetate in petroleum ether to provide the pure product. When chiral (S)-2-phenyl-N-tosylazetidine was used, non-racemic 4 was obtained. Greater enantioselectivity was observed when aldehydes or ketones were used as the solvent. In the case of ketones, the cycloaddition product was found to be very unstable and during work-up was hydrolyzed to the substituted 3-amino-1-phenyl-1-propanol.
42. 3), with 75% ee [Chiracel AD-H column; hexane/isopropanol, 90:10; flow rate = 1.0 mL/min].
43. Crystallographic data of compound 4c in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 643311. Copies of the data can be obtained free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk].
44. Enantiomerically pure (S)-1 and 11 were prepared using our reported method:. Ghorai M.K., Das K., and Kumar A. Tetrahedron Lett. 48 (2007) 2471-2475
45. ++1).
46. 2, racemization of the starting azetidine (S)-1 is appreciable and hence the enantioselectivity is reduced.
47. Although 12 and 13 are inseparable by TLC or simple column chromatography, they were separated by HPLC.