A convenient new procedure for the construction of highly substituted acetates. Reductive alkylation of α-cyano esters

Tetrahedron Letters

Volumn 38, Issue 44, 1997, Pages 7713-7716

  Shia, Kak Shan ^a   Chang, Nien Yin ^a   Yip, Judy ^b   Liu, Hsing Jang ^b  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; NITRILE;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; REDUCTION; SYNTHESIS;

EID: 0030656469     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10063-6     Document Type: Article

References (20)

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9. For preparation of lithium naphthalenide in situ or as a stock solution see ref. 4.
10. Liu, H. J.; Yip, J.; Shia, K. S. Tetrahedron Lett. 1997, 2253-2256.
11. Flash chromatography was carried out on silica gel, eluting first with n-hexane to remove naphthalene and then a solution of 2-4% ethyl acetate in n-hexane to effect isolation of the product.
12. 4
13. Yields are for isolated products and unoptimized.
14. Oediger, H.; Moller, F. Liebigs Ann. Chem. 1976, 348-351.
15. The work-up procedure was modified as follows. After the reaction, water (same volumn as that of dimethyl formamide used for the reaction) was added and the resulting solution extracted with ether. The combined extracts were washed with 2N hydrochloric acid, water and then dried with magnesium sulfate, filtered and concentrated to give the crude product. This procedure resulted in considerable improvement (> 20%) of yields.
16. Ono, N.; Yoshimura, T.; Saito, T.; Tamura, R.; Tanikaga, R.; Kaji, A. Bull. Chem. Soc. Jpn. 1979, 1716-1719.
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20. We are currently studying the reductive alkylation of α-cyano ketones. Preliminary results are promising. This investigation will be reported elsewhere in due course.