Reductive alkylation of α-cyano ketones induced by samarium iodide

Tetrahedron Letters

Volumn 40, Issue 39, 1999, Pages 7055-7058

  Zhu, Jia Liang ^a   Shia, Kak Shan ^b   Liu, Hsing Jang ^a,b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

Alkylation; Cyano compounds; Reduction; Samarium; Samarium compounds

Indexed keywords

CYANOKETONE; IODIDE; REAGENT; SAMARIUM;

ALKYLATION; ARTICLE; CHEMICAL REACTION; REDUCTION;

EID: 0033600829     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01470-7     Document Type: Article

References (23)

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8. 8. For preparation of samarium iodide as a stock solution, see: Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693-2698.
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10. 10. Shabangi, M.; Flowers, R. A. Tetrahedron Lett. 1997, 38, 1137-1140. (equation presented) Reductive alkylation of α-cyano ketones with samarium iodide a A single diastereomer was formed. Its stereochemistry remains to be determined. b Two diastereomers were formed in a ratio of 1:1
11. 11. The use of a less amount of the reagent often resulted in incompletion of the reaction under the specified conditions. The amount of the alkylating agent was adjusted accordingly to cover the expected side reactions with cyanide and with the excess samarium iodide, such as reductive dehalogenation.
12. 12. The stereochemistry of this compound was confirmed by NOE experiments. Results are compiled in Fig. 1. Where applicable, the stereochemistry of other products listed in Table 1 was also deduced in a similar fashion.
13. 13. Yields are for purified products and unoptimized.
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