Diastereoselective Addition of Allyltitanocenes to Cyclic Enones

The reaction of allyltitanocenes with five- to seven-membered cyclic enones proceeded with good to high diastereoselectivity depending on the ring size of enones. The stereochemistry of the major isomers produced by the reaction of cinnamyltitanocene was opposite to that of crotyltitanocene.

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Published in:Organic letters Vol. 14; no. 8; pp. 2042 - 2045
Main Authors: Takeda, Takeshi, Nishimura, Takuya, Yoshida, Satoshi, Saiki, Fumiya, Tajima, Yuki, Tsubouchi, Akira
Format: Journal Article
Language:English
Published: United States American Chemical Society 20-04-2012
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Abstract The reaction of allyltitanocenes with five- to seven-membered cyclic enones proceeded with good to high diastereoselectivity depending on the ring size of enones. The stereochemistry of the major isomers produced by the reaction of cinnamyltitanocene was opposite to that of crotyltitanocene.
AbstractList The reaction of allyltitanocenes with five- to seven-membered cyclic enones proceeded with good to high diastereoselectivity depending on the ring size of enones. The stereochemistry of the major isomers produced by the reaction of cinnamyltitanocene was opposite to that of crotyltitanocene.
Author Yoshida, Satoshi
Tsubouchi, Akira
Takeda, Takeshi
Tajima, Yuki
Nishimura, Takuya
Saiki, Fumiya
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Cites_doi 10.1002/anie.200700975
10.1021/jo9723016
10.1021/ja910593w
10.1002/anie.200901384
10.1002/cber.19901230127
10.1002/anie.200603659
10.1021/ja062528v
10.1021/ja071380s
10.1002/anie.201003813
10.1021/ja0274047
10.1246/cl.1980.993
10.1002/chem.201000101
10.1002/chem.200802340
10.1016/j.tet.2011.10.002
10.1021/ja804182j
10.1016/S0040-4039(99)01982-6
10.1021/ja047200l
10.1021/ol900599q
10.1021/ol702607t
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References Dunet G. (ref6/cit6b) 2008; 10
Katkin A. N. (ref7/cit7) 1999; 40
Althaus M. (ref3/cit3h) 2010; 132
Yasuda M. (ref4/cit4a) 2002; 124
O’Brien A. G. (ref1/cit1) 2011; 67
Schmidtmann E. S. (ref4/cit4b) 2009; 48
Fang G. Y. (ref3/cit3d) 2007; 46
Takaki K. (ref9/cit9) 1998; 63
Takeda T. (ref2/cit2b) 2010; 16
Tietze L. F. (ref5/cit5) 2006; 128
Ren H. (ref6/cit6a) 2007; 129
Yatsumonji Y. (ref2/cit2a) 2009; 15
Carosi L. (ref3/cit3e) 2007; 46
Schneider U. (ref3/cit3f) 2008; 130
Wada R. (ref3/cit3c) 2004; 126
Yamaguchi M. (ref3/cit3a) 1980
Nowrouzi F. (ref3/cit3g) 2009; 11
Peng Z. (ref8/cit8) 2010; 49
Hoffmann R. W. (ref3/cit3b) 1990; 123
References_xml – volume: 46
  start-page: 5913
  year: 2007
  ident: ref3/cit3e
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.200700975
  contributor:
    fullname: Carosi L.
– volume: 63
  start-page: 4299
  year: 1998
  ident: ref9/cit9
  publication-title: J. Org. Chem.
  doi: 10.1021/jo9723016
  contributor:
    fullname: Takaki K.
– volume: 132
  start-page: 4025
  year: 2010
  ident: ref3/cit3h
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja910593w
  contributor:
    fullname: Althaus M.
– volume: 48
  start-page: 4634
  year: 2009
  ident: ref4/cit4b
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.200901384
  contributor:
    fullname: Schmidtmann E. S.
– volume: 123
  start-page: 145
  year: 1990
  ident: ref3/cit3b
  publication-title: Chem. Ber.
  doi: 10.1002/cber.19901230127
  contributor:
    fullname: Hoffmann R. W.
– volume: 46
  start-page: 359
  year: 2007
  ident: ref3/cit3d
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.200603659
  contributor:
    fullname: Fang G. Y.
– volume: 128
  start-page: 11483
  year: 2006
  ident: ref5/cit5
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja062528v
  contributor:
    fullname: Tietze L. F.
– volume: 129
  start-page: 5376
  year: 2007
  ident: ref6/cit6a
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja071380s
  contributor:
    fullname: Ren H.
– volume: 49
  start-page: 8516
  year: 2010
  ident: ref8/cit8
  publication-title: Angew. Chem., Int. Ed.
  doi: 10.1002/anie.201003813
  contributor:
    fullname: Peng Z.
– volume: 124
  start-page: 13442
  year: 2002
  ident: ref4/cit4a
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja0274047
  contributor:
    fullname: Yasuda M.
– start-page: 993
  year: 1980
  ident: ref3/cit3a
  publication-title: Chem. Lett.
  doi: 10.1246/cl.1980.993
  contributor:
    fullname: Yamaguchi M.
– volume: 16
  start-page: 4729
  year: 2010
  ident: ref2/cit2b
  publication-title: Chem.—Eur. J.
  doi: 10.1002/chem.201000101
  contributor:
    fullname: Takeda T.
– volume: 15
  start-page: 2680
  year: 2009
  ident: ref2/cit2a
  publication-title: Chem.—Eur. J.
  doi: 10.1002/chem.200802340
  contributor:
    fullname: Yatsumonji Y.
– volume: 67
  start-page: 9639
  year: 2011
  ident: ref1/cit1
  publication-title: Tetrahedron
  doi: 10.1016/j.tet.2011.10.002
  contributor:
    fullname: O’Brien A. G.
– volume: 130
  start-page: 13824
  year: 2008
  ident: ref3/cit3f
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja804182j
  contributor:
    fullname: Schneider U.
– volume: 40
  start-page: 9353
  year: 1999
  ident: ref7/cit7
  publication-title: Tetrahedron Lett.
  doi: 10.1016/S0040-4039(99)01982-6
  contributor:
    fullname: Katkin A. N.
– volume: 126
  start-page: 8910
  year: 2004
  ident: ref3/cit3c
  publication-title: J. Am. Chem. Soc.
  doi: 10.1021/ja047200l
  contributor:
    fullname: Wada R.
– volume: 11
  start-page: 2631
  year: 2009
  ident: ref3/cit3g
  publication-title: Org. Lett.
  doi: 10.1021/ol900599q
  contributor:
    fullname: Nowrouzi F.
– volume: 10
  start-page: 117
  year: 2008
  ident: ref6/cit6b
  publication-title: Org. Lett.
  doi: 10.1021/ol702607t
  contributor:
    fullname: Dunet G.
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Title Diastereoselective Addition of Allyltitanocenes to Cyclic Enones
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