Room-temperature highly diastereoselective Zn-mediated allylation of chiral N-tert-butanesulfinyl imines: Remarkable reaction condition controlled stereoselectivity reversal

Organic Letters

Volumn 8, Issue 21, 2006, Pages 4979-4982

  Sun, Xing Wen ^a   Xu, Ming Hua ^a,b   Lin, Guo Qiang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750316213     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062216x     Document Type: Article

References (38)

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35. The configuration was assigned by comparison with literature data for the free homoallylic amine; see the Supporting Information for details.
36. 2O has a substantial influence on the reaction yield and diastereoselectivity; see the Supporting Information for details. Also, a similar water effect was found for additions to imines, see refs 2a and 6c.
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38. (b) Berger, R.; Duff, K.; Leighton, J. L. J. Am. Chem. Soc. 2004, 126, 5686. For examples of allylmagnesium bromide addition to N-sulfinyl ketoimines, see ref 2e,f.