Abstract
A new organocatalyst derived from proline has been developed and shown to be an efficient catalyst for asymmetric Michael addition reactions of cyclohexanone to nitroolefins with high diastereo- and enantio -selectivities. (syn: anti up to 99:1, ee. up to 93%.).
References
1.
Dalko P.I.
, Angew. Chem. Int. Ed. , 2004 , 43 , 5138 .
2.
Berner O.M.
,
Tedeschi L.
, and
Enders D.
, Eur. J. Org. Chem. , 2002 , 1877 .
3.
Ono N.
, The nitro group in organic synthesis Wiley-VCH , New York , 2001 .
4.
Sakthivel K.
,
Notz W.
,
Bui T.
,
Barbas C.F.
III
, J. Am. Chem. Soc. , 2001 , 123 , 5260
5.
List B.
,
Pojarliev P.
,
Martin H.J.
, Org. Lett. , 2001 , 3 , 2423 .
6.
Ishii T.
,
Fujioka S.
,
Sekiguchi Y.
, and
Kotsuki H.
, J. Am. Chem. Soc. , 2004 , 126 , 9558 .
7.
Betancort J.M.
,
Sakthivel K.
,
Thayumanavan R.
,
Tanaka F.
, and
Barbas C.F.
III
Synthesis , 2004 , 1509 .
8.
Alexakis A.
, and
Andrey O.
, Org. Lett. , 2002 , 4 , 3611 .
9.
Cobb A.J. A
,
Longbottom D.A.
,
Shaw D.M.
, and
Ley S.V.
, Chem. Commun. , 2004 , 1808 .
10.
Cobb A.J.A.
,
Shaw D.M.
,
Longbottom D.A.
,
Gold J.B.
, and
Ley S.V.
, Org. Biomol. Chem. , 2005 , 3 , 84 .
11.
Wang J.
,
Li H.
,
Lou B.
,
Zu L.
,
Guo H.
, and
Wang W.
, Chem.-Eur. J. , 2006 , 12 , 4321 .
12.
Vishnumaya
, and
Singh V.K.
, Org. Lett. , 2007 , 9 , 1117 .
13.
Xu D.-Q.
,
Wang L.-P.
,
Luo S.-P.
,
Wang Y.-F.
,
Zhang S.
, and
Xu Z.-Y.
, Eur. J. Org. Chem. , 2008 , 1049 .
14.
Bukuo N.
,
Zhang Q.-Y.
,
Kritanjali D.
, and
Allan D.H.
, Org. Lett. , 2009 , 11 , 1037 .
15.
Wang L.
,
Liu J.
,
Miao T.
,
Zhou W.
,
Li P.
,
Ren K.
, and
Zhang X.
, Adv. Synth. Catal. , 2010 , 352 , 1629 .
16.
Cao X.
,
Wang G.
,
Zhang R.
,
Wei Y.
,
Wang W.
,
Sun H.
, and
Chen L.
Org. Biomol. Chem. , 2011 , 9 , 6487 .
17.
Mase N.
,
Thayumanavan R.
,
Tanaka F.
, and
Barbas C.F.
III
, Org. Lett. , 2004 , 6 , 2527 .
18.
Zhu M.
,
Cun L.
,
Mi A.
,
Jiang Y.
, and
Gong L.
, Tetrahedron: Asymm. , 2006 , 17 , 491 .
19.
Chuan Y.
,
Chen G.
, and
Peng Y.
, Tetraheron Lett. , 2009 , 25 , 3054 .
