Samarium diiodide-induced asymmetric synthesis of optically pure unsymmetrical vicinal diamines by reductive cross-coupling of nitrones with N-tert-butanesulfinyl imines

Organic Letters

Volumn 6, Issue 22, 2004, Pages 3953-3956

  Zhong, Yu Wu ^a   Xu, Ming Hua ^a   Lin, Guo Qiang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE DERIVATIVE; IMINE; NITRONE DERIVATIVE; SAMARIUM DIIODIDE;

ALKYLATION; ARTICLE; CHEMICAL BOND; ENANTIOSELECTIVITY; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 8744311540     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048444d     Document Type: Article

References (43)

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37. No other stereoisomer was observed according to 1H NMR analysis of the crude material.
38. For X-ray structure-related data, see Supporting Information.
39. In most cases in Table 2, the yields of most of the cross-coupling reactions are modest mainly due to the remaining starting material N-tert-butanesulfinyl imines.
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42. Chiral HPLC showed 99.6% ee of its diacetate derivative. For comparison, (S,S)-4 was also prepared by the reaction of nitrone 1 with (S)-N-tert- butanesulfinyl imine 2; see Supporting Information for details.
43. 2 under similar conditions. Thus, this suggests that a radical-based addition of the nitrone radical to the imine followed by further reduction of the nitrogen-based radical may not be preferred.