Abstract
Copper-catalyzed asymmetric 1,4-addition of diethylzinc to β,γ-unsaturated α-imino esters 1 using a copper-phosphoramidite complex affords enantiomerically enriched γ-functionalized α-dehydroamino esters 2 .
Key words
amino acids - asymmetric catalysis - imines - Michael addition - organometallics
References
1a Zhang W.
Zhang X.
J. Org. Chem.
2007,
72:
1020
1b Hu X.-P.
Huang J.-D.
Zeng Q.-H.
Zheng Z.
Chem. Commun.
2006,
293
1c Hoen R.
Van den Berg M.
Bernsmann H.
Minnaard AJ.
De Vries JG.
Feringa BL.
Org. Lett.
2004,
6:
1433
2a Cerić H.
Kovačević M.
Šindler-Kulyk M.
Tetrahedron
2000,
56:
3985
2b Hou D.
Mas JL.
Chan TM.
Wong YS.
Steinman M.
McPhail AT.
Bioorg. Med. Chem. Lett.
1993,
3:
2171
2c Farina V.
Hauck SI.
Walker DG.
Synlett
1992,
76
3a El Ashry ESH.
Ramadan ES.
Abdel Hamid H.
Hagar M.
Lett. Org. Chem.
2005,
2:
415
3b Cvetovich RJ.
Pipik B.
Hartner FW.
Grabowski EJJ.
Tetrahedron Lett.
2003,
44:
5867
3c Nagasaki A.
Adachi Y.
Yonezawa Y.
Shin C.-G.
Heterocycles
2003,
60:
321
3d Arnold Z.
Synthesis
1990,
39
3e Breslow R.
Canary JW.
Varney M.
Waddell ST.
Yang D.
J. Am. Chem. Soc.
1990,
112:
5212
4a RajanBabu TV.
Yan YY.
Shin S.
Curr. Org. Chem.
2003,
7:
1759
4b Drexler HJ.
You J.
Zhang S.
Fisher C.
Bauman W.
Spannenberg A.
Heller DT.
Org. Process Res. Dev.
2003,
7:
355
4c Brunner H.
Curr. Org. Chem.
2002,
6:
441
4d Schmidt U.
Lieberknecht A.
Wild J.
Synthesis
1988,
159
5a Broda MA.
Siodak D.
Rzeszotarska B.
J. Pept. Sci.
2005,
11:
546
5b Mathur P.
Ramakumar S.
Chauhan VS.
Biopolymers
2004,
76:
150
5c Vijayaraghavan R.
Kumar P.
Dey S.
Singh TP.
J. Pept. Res.
2003,
62:
63
6a Chen D.
Guo L.
Liu J.
Kirtane S.
Cannon JF.
Li G.
Org. Lett.
2005,
7:
921
6b Sai H.
Ogiku T.
Ohmizu H.
Synthesis
2003,
201
6c Ferreira PMT.
Maia HLS.
Monteiro LS.
Sacramento J.
J. Chem. Soc., Perkin Trans. 1
1999,
3697
6d Stohlmeyer MM.
Tanaka H.
Wandless TJ.
J. Am. Chem. Soc.
1999,
121:
6100
6e Ferreira PMT.
Maia HLS.
Montiro LS.
Tetrahedron Lett.
1998,
39:
9575
7 Groundwater PW.
Sharif T.
Arany A.
Hibbs DE.
Hursthouse MB.
Nyerges M.
Tetrahedron Lett.
1998,
39:
1433
8 Davis FA.
Liu H.
Liang C.-H.
Venkat Reddy G.
Zhang Y.
Fang T.
Titus DD.
J. Org. Chem.
1999,
64:
8929
9 Trost BM.
Dake GR.
J. Am. Chem. Soc.
1997,
119:
7595
10 Schmidt U.
Griesser H.
Leitenberger V.
Lieberknecht A.
Mangold R.
Meyer R.
Riedl B.
Synthesis
1992,
487
11a Palacios F.
Vicario J.
Maliszewska A.
Aparicio D.
J. Org. Chem.
2007,
72:
2682
11b Palacios F.
Vicario J.
Aparicio D.
J. Org. Chem.
2006,
71:
7690
11c Palacios F.
Alonso C.
Rubiales G.
Villegas M.
Tetrahedron
2005,
61:
2779
11d Palacios F.
Ochoa de Retana AM.
Pascual S.
Oyarzabal J.
J. Org. Chem.
2004,
69:
8767
11e Palacios F.
Ochoa de Retana AM.
Pascual S.
Oyarzabal J.
Org. Lett.
2002,
4:
769
12 Palacios F.
Vicario J.
Org. Lett.
2006,
8:
5405
13 The absolute configuration of the stereogenic center of 2 was established by comparison of the rotary power of the known carboxylic acid resulting from ozonolysis and subsequent oxidation of the intermediate aldehyde.
14 The conventional process involves the addition of a solution of 1-azadiene 1 to a toluene solution of diethylzinc together with the copper catalyst.
