A versatile route to β-enamino esters by acylation of lithium enamines with diethyl carbonate or benzyl chloroformate

作者: Giuseppe Bartoli , Cristina Cimarelli , Renato Dalpozzo , Gianni Palmieri

DOI: 10.1016/0040-4020(95)00476-O

关键词:

摘要: Abstract A versatile route to β-enamino esters 1, using accessible starting materials, was developed. Lithiated enamines are allowed react with diethyl carbonate or benzyl chloroformate the formation of 1a 1b. The reaction is rather general from a wide array ketimines and aldimines. Products included cyclic 1aa-ac, very useful for synthesis natural products.

参考文章(23)
S. Danishefsky, Sarah J. Etheredge, Synthesis and biological evaluation of DE-AB-camptothecin. Journal of Organic Chemistry. ,vol. 39, pp. 3430- 3432 ,(1974) , 10.1021/JO00937A034
Duy H. Hua, Shou Wu Miao, S. Narasimha Bharathi, Takeshi Katsuhira, Ana A. Bravo, Selective nucleophilic addition reactions of alkyllithium reagents with N-(trimethylsilyl)lactams. Synthesis of cyclic ketimines Journal of Organic Chemistry. ,vol. 55, pp. 3682- 3684 ,(1990) , 10.1021/JO00298A062
Giuseppe Bartoli, Cristina Cimarelli, Enrico Marcantoni, Gianni Palmieri, Marino Petrini, Chemo- and Diastereoselective Reduction of .beta.-Enamino Esters: A Convenient Synthesis of Both cis- and trans-.gamma.-Amino Alcohols and .beta.-Amino Esters Journal of Organic Chemistry. ,vol. 59, pp. 5328- 5335 ,(1994) , 10.1021/JO00097A039
Cristina Cimarelli, Gianni Palmieri, Giuseppe Bartoli, Diastereo and enantioselective entry to β-amino esters by hydride reduction of homochiral β-enamino esters Tetrahedron-asymmetry. ,vol. 5, pp. 1455- 1458 ,(1994) , 10.1016/0957-4166(94)80111-8
M. B. Eleveld, H. Hogeveen, E. P. Schudde, DIASTEREOSELECTIVE SYNTHESIS OF CHIRAL SECONDARY-AMINES WITH 2 CHIRAL CENTERS DIRECTLY ATTACHED TO THE NITROGEN ATOM Journal of Organic Chemistry. ,vol. 51, pp. 3635- 3642 ,(1986) , 10.1021/JO00369A016
William D. Lubell, Masato Kitamura, Ryoji Noyori, Enantioselective synthesis of β-amino acids based on BINAP—ruthenium(II) catalyzed hydrogenation Tetrahedron: Asymmetry. ,vol. 2, pp. 543- 554 ,(1991) , 10.1016/S0957-4166(00)86107-8
G. Wittig, H. Reiff, Directed Aldol Condensations Angewandte Chemie. ,vol. 7, pp. 7- 14 ,(1963) , 10.1002/ANIE.196800071