Abstract
The N-benzoyl of α,β-dehydroamino acids that were obtained by condensation of N-benzoylglycine and an aldehyde, were esterified with an alcohol in high yield using cyclohexyl isocyanide to activate the carboxylic acid under neutral conditions.
References
1.
Aguado G.P.
,
Moglioni A.G.
, and
Ortuno R.M.
, Tetrahedron Asymm. , 2003 , 14 , 217 .
2.
Williams R.M.
, Synthesis of optically active α-amino acids. Pergamon Press , 1989 , Oxford , p. 1 .
3.
O'Donnell M.J.
, and
Bennett W.D.
, Tetrahedron , 1988 , 44 , 5389 .
4.
Ikegami S.
,
Uchiyama H.
,
Hayama T.
,
Katsuki T.
, and
Yamaguchi M.
, Tetrahedron , 1988 , 44 , 5333 .
5.
Coghlan P.A.
, and
Easton C.J.
, Tetrahedron Lett. , 1999 , 40 , 4745 .
6.
Thormann M.
, and
Hofmann H.J.
, J. Mol. Struct. , 1998 , 431 , 79 .
7.
Palmer D.E.
,
Pattaroni C.
,
Nunami K.
,
Chadha R.K.
,
Goodman M.
,
Wakamiya T.
,
Fukase K.
,
Horimoto S.
,
Kitazawa M.
,
Fujita H.
,
Kubo A.
, and
Shiba T.
, J. Am. Chem. Soc. , 1992 , 114 , 5634 .
8.
Tungler A.
, and
Fogassy G.
, J. Mol. Catalysis , 2001 , 173 , 231 .
9.
Adamczyk M.
,
Akireddy S.R.
, and
Reddy R.E.
, Tetrahedron , 2002 , 58 , 6951 , 6951.
10.
Aguado G.P.
,
Alvarez-Larena A.
,
Illa O.
,
Moglioni A.G.
, and
Ortuno R.M.
, Tetrahedron Asymm. , 2001 , 12 , 25 .
11.
Wang W.
,
Xiong C.
,
Zhang J.
, and
Hruby V.J.
, Tetrahedron , 2002 , 58 , 3101 .
12.
Mazurkiewicz R.
,
Kuz'nik A.
,
Grymel M.
, and
Kuznik N.
, Monatsh. Chem. , 2004 , 135 , 807 .
13.
Schmidt U.
,
Lieberknecht A.
,
Schanbacher U.
,
Beuttler T.
, and
Wild J.
, Angew. Chem. Int. Ed Engl. , 1982 , 21 , 776 .
14.
Schmidt U.
,
Lieberknecht A.
, and
Wild J.
, Synthesis , 1984 , 1 , 53 .
15.
Schmidt U.
,
Weller D.
,
Holder A.
, and
Lieberknecht A.
, Tetrahedron Lett. , 1988 , 29 , 3227 .
16.
Schmidt U.
,
Lieberknecht A.
, and
Wild J.
, Synthesis , 1988 , 1 , 159 .
17.
Ugi I
, Isonitrile chemistry. Academic Press , New York , Chap. 4, pp. 65 –92 .
18.
Yavari I.
,
Nori Shargh D.
,
Fallah H.
, and
Shaidaii B.
, J. Chem. Res. , 1996 , 146 .
19.
Mosslemin M.H.
,
Yavari I.
,
Anary-Abbasinejad M.
, and
Nateghi M.R.
, J. Fluorine Chem. , 2004 , 125 , 1497 .
20.
Shaabani A.
,
Soleimani E.
, and
Rezayan A.H.
, Tetrahedron Lett. , 2007 , 48 , 2185
21.
Shaabani A.
,
Soleimani E.
, and
Rezayan A.H.
, Tetrahedron Lett. , 2007 , 48 , 6137 .
22.
Mizung Y.
, and
Kobayashi J.
, J. Chem. Soc. Chem. Commun. , 1974 , 997 .
23.
Schollkopf U.
, and
Meyer R.
, Liebigs Ann. Chem. , 1981 , 1469 .
24.
Cativiela C.
,
Diaz de Villegas M.D.
,
Mayoral J.A.
, and
Melendez E.
, Synthesis , 1983 , 11 , 899 .
25.
Gelbard G.
, and
Kagan H.B.
, Tetrahedron , 1976 , 32 , 233 .
26.
Belokon Y.N.
,
Chernoglazova N.I.
,
Bakhmutov V.I.
,
Garbalinskaya N.S.
, and
Belikov V.M.
, Russ. Chem. Bull. , 1987 , 2595 .
27.
Ma Z.H.
,
Liu C.
,
Zhao Y.H.
,
Li W.
, and
Wang J.B.
, Chinese Chem. Lett. , 2002 , 13 , 721 .
28.
Li J.
, and
Sha W.
, Molecules , 2008 , 13 , 1111 .
29.
Jursic B.S.
,
Sagiraju S.
,
Ancalade D.K.
,
Clark T.
, and
Stevens E.D.
, Synthetic Commun. , 2007 , 37 , 1709 .
30.
Eliel E.L.
,
Wilen S.H.
, and
Mander L.N.
, Stereochemistry of organic compounds , Wiley , New York , 1994 , p. 569 .
31.
Kumar P.
,
Mishra H.D.
, and
Mukerjee A.M.
, Synthesis 1980 , 836 .
32.
Ugi I.
, Pure Appl. Chem. , 2001 , 77 , 187 .
33.
Bagley M.C.
,
Cale J.W.
, and
Bower J.
, Chem. Commun. , 2002 , 1682 .
34.
Bora U.
,
Saikia A.
, and
Boruah R.C.
, Org. Lett. , 2003 , 5 , 435 .
35.
Yavari I.
,
Djahaniani H.
, and
Nasiri F.
, Tetrahedron , 2003 , 59 , 9409 .