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Synlett 2006(2): 181-193
DOI: 10.1055/s-2006-926220
DOI: 10.1055/s-2006-926220
ACCOUNT
© Georg Thieme Verlag Stuttgart · New York
Towards Reaction Selectivities of Imines and Aziridines
Weitere Informationen
Received
31 July 2005
Publikationsdatum:
24. Januar 2006 (online)
Publikationsverlauf
Publikationsdatum:
24. Januar 2006 (online)
Abstract
Several simple and convenient transformations of imines and aziridines under mild conditions have been developed, rendering access to several kinds of β-amino derivatives, α-amino nitriles and phosphonates, aziridines, and conjugated dienes from imines and aziridines under neutral and metal-free conditions very conveniently. High stereoselectivities are realized in most reactions based upon mechanistic considerations.
Key words
transformations - imines - aziridines - mild conditions
- For some reviews of imines and aziridines:
-
2a
Tanner D. Angew. Chem., Int. Ed. Engl. 1994, 33: 599 -
2b
Li AH.Dai LX.Aggarwal VK. Chem. Rev. 1997, 97: 2431 -
2c
Bloch R. Chem. Rev. 1998, 98: 1407 - 3
The Chemistry of the Carbon-Nitrogen Double Bond
Patai S. Wiley; London: 1970. p.235 - 4
Li AH.Dai LX.Hou XL.Chen MB. J. Org. Chem. 1996, 61: 4641 - 5
Li AH.Dai LX.Hou XL. J. Chem. Soc., Perkin Trans. 1 1996, 867 -
6a
Li AH.Zhou YG.Dai LX.Hou XL.Xia LJ.Lin L. Angew. Chem., Int. Ed. Engl. 1997, 36: 1317 -
6b
Li AH.Zhou YG.Dai LX.Hou XL.Xia LJ.Tang MH. J. Org. Chem. 1998, 63: 4338 -
7a
Keck GE.Enholm EJ. J. Org. Chem. 1985, 50: 146 -
7b
Wang DK.Dai LX.Hou XL. Tetrahedron Lett. 1995, 36: 8649 - 8
Wang DK.Dai LX.Hou XL. Chem. Commun. 1997, 1231 -
9a
Mohan JM.Uphade BS.Choudhary VR.Ravindranathan Y.Sudalai A. Chem. Commun. 1997, 1429 -
9b
Matano Y.Yoshimune M.Suzuki H. J. Org. Chem. 1995, 60: 4663 -
9c
McLaren AB.Sweeney JB. Org. Lett. 1999, 1: 1339 -
9d
Aggarwal VK.Charmant JPH.Ciampi C.Hornby JM.O’Brien CJ.Hynd G.Parsons R. J. Chem. Soc., Perkin Trans. 1 2001, 3159 -
10a
Tang Y.HuangY Z.Dai LX.Sun J.Xia W. J. Org. Chem. 1997, 62: 954 -
10b
Ye S.Tang Y.Dai LX. J. Org. Chem. 2000, 65: 6257 -
10c
Ye S.Huang ZZ.Xia CA.Tang Y.Dai LX. J. Am. Chem. Soc. 2002, 124: 2432 -
10d
Liao WW.Li K.Tang Y. J. Am. Chem. Soc. 2003, 125: 13030 -
11a
Zhou YG.Li AH.Hou XL.Dai LX. Chem. Commun. 1996, 1353 -
11b
Zhou YG.Li AH.Dai LX.Hou XL. Acta Chim. Sinica 2000, 58: 473 - 12
Aggarwal VK.Winn CL. Acc. Chem. Res. 2004, 37: 611 -
13a
Hou XL.Yang XF.Dai LX.Chen XF. Chem. Commun. 1998, 747 -
13b
Yang XF.Zhang MJ.Hou XL.Dai LX. J. Org. Chem. 2002, 67: 8097 -
14a
Johnson CR.Schroeck CW. J. Am. Chem. Soc. 1971, 93: 5303 -
14b
Johnson CR.Schroeck CW.Shanklin JR. J. Am. Chem. Soc. 1973, 95: 7424 - 15
Hosomi A.Shirahata A.Sakurai H. Tetrahedron Lett. 1978, 19: 3043 -
16a
Kira M.Hino T.Sakurai H. Chem. Lett. 1991, 277 -
16b
Pilcher AS.DeShong P. J. Org. Chem. 1996, 61: 6901 - 17
Wang DK.Zhou YG.Tang Y.Hou XL.Dai LX. J. Org. Chem. 1999, 64: 4233 - 18
Sakurai H.Hosomi A.Saito M.Sasaki K.Iguchi H.Sasaki J.Araki Y. Tetrahedron 1983, 39: 883 - 19
Gröger H. Chem. Rev. 2003, 103: 2795 - 20
Wu J.Hou XL.Dai LX. J. Org. Chem. 2000, 65: 1344 - 21
Li BF.Yuan K.Zhang MJ.Wu H.Dai LX.Wang QR.Hou XL. J. Org. Chem. 2003, 68: 6264 - 22
Davis FA.Reddy RE.Portonovo P. Tetrahedron Lett. 1994, 35: 9351 - 23
Davis FA.Lee S.Zhang H.Fanelli DL. J. Org. Chem. 2000, 65: 8704 - 24
Li BF.Zhang MJ.Hou XL.Dai LX. J. Org. Chem. 2002, 67: 2902 - 25
Lefebvre IM.Evans SA. J. Org. Chem. 1997, 62: 7532 - For reviews see:
-
26a
Ellman JA.Owens TD.Tang TP. Acc. Chem. Res. 2002, 35: 984 -
26b
Zhou P.Chen BC.Davis FA. Tetrahedron 2004, 60: 8003 -
27a
Hua DH.Miao SW.Chen JS.Iguchi S. J. Org. Chem. 1991, 56: 4 -
27b
Harmata M.Kahraman M.Jones DE.Pavri N.Weatherwax SE. Tetrahedron 1998, 54: 9995 -
27c
Davis FA.Lee S.Zhang HM.Fanelli DL. J. Org. Chem. 2000, 65: 8704 -
27d
Davis FA.Ramachandar T.Liu H. Org. Lett. 2004, 6: 3393 - 28
Wu J.Hou XL.Dai LX. J. Chem. Soc., Perkin Trans. 1 2001, 1314 - 29
Li BF.Yuan K.Dai LX.Hou XL. Synlett 2005, 535 -
30a
Stamm H. J. Prakt. Chem. 1999, 319 -
30b
Hu XE. Tetrahedron 2004, 60: 2701 - 31
Fan RH.Hou XL.Dai LX. J. Org. Chem. 2004, 69: 689 - 32
Ding CH.Dai LX.Hou XL. Synlett 2004, 2218 -
33a
Prasad BAB.Sekar G.Singh VK. Tetrahedron Lett. 2000, 41: 4677 -
33b
Ding, C. H.; Hou, X. L. unpublished work.
- 34
Fan RH.Hou XL. Org. Biomol. Chem. 2003, 1: 1565 - 35
Kobayashi S.Tsuchiya Y.Mukaiyama T. Chem. Lett. 1991, 537 - 36
Hou XL.Fan RH.Dai LX. J. Org. Chem. 2002, 67: 5295 - 37
Fan RH.Hou XL. J. Org. Chem. 2003, 68: 726 - 38
Wittig G.Hagg W. Chem. Ber. 1955, 88: 1654 - For some examples see:
-
39a
Aggarwal VK. Synlett 1998, 329 -
39b
Aggarwal VK.Alonso E.Hynd G.Lydon KM.Palmer MJ.Porcelloni M.Studley JR. Angew. Chem. Int. Ed. 2001, 40: 1430 -
39c
Huang ZZ.Ye S.Xia W.Tang Y. Chem. Commun. 2001, 1384 -
39d
Huang ZZ.Ye S.Xia W.Yu YH.Tang Y. J. Org. Chem. 2002, 67: 3096 -
39e
Aggarwal VK.Harvey JN.Richardson J. J. Am. Chem. Soc. 2002, 124: 5747 -
39f
Balema VP.Wiench JW.Pruski M.Pecharsky VK. J. Am. Chem. Soc. 2002, 124: 6244 -
39g
Du YS.Lu XY.Zhang CM. Angew. Chem. Int. Ed. 2003, 42: 1035 -
39h
Li K.Ran L.Yu YH.Tang Y. J. Org. Chem. 2004, 69: 3986 - 40
Dellaria JF.Sallin KJ. Tetrahedron Lett. 1990, 2661 - 41
Fan RH.Hou XL.Dai LX. J. Org. Chem. 2004, 69: 689 - 42
Vedejs E.Snoble KAJ.Fuchs PL. J. Org. Chem. 1973, 38: 1178 - 43
Schweizer EE.Smucker LD.Votral RJ. J. Org. Chem. 1966, 31: 467 - 44
Arisawa K.Yamaguchi M. J. Am. Chem. Soc. 2000, 122: 2387 - For some examples see:
-
45a
Osborn HM.Sweeney JB.Howson B. Synlett 1993, 675 -
45b
Dubois L.Mehta A.Tourette E. J. Org. Chem. 1994, 59: 434 -
45c
Müller P.Nury P. Org. Lett. 1999, 1: 439 -
45d
Ding CH.Dai LX.Hou XL. Synlett 2004, 1691 - For some examples see:
-
46a
Veenstra SJ.Kinderman SS. Synlett 2001, 1109 -
46b
Hou XL.Luo YM.Yuan K.Dai LX. J. Chem. Soc., Perkin Trans. 1 2002, 1487 -
46c
Kochi T.Ellman JA. J. Am. Chem. Soc. 2004, 126: 15652
References and Notes
Current address: Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, P. R. of China