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Synthesis 2007(24): 3877-3885
DOI: 10.1055/s-2007-990917
DOI: 10.1055/s-2007-990917
PAPER
© Georg Thieme Verlag Stuttgart · New York
New Paracyclophane Phosphine for Highly Enantioselective Ruthenium-Catalyzed Hydrogenation of Prochiral Ketones
Further Information
Received
21 August 2007
Publication Date:
28 November 2007 (online)
Publication History
Publication Date:
28 November 2007 (online)
Abstract
The synthesis of a new paracyclophane phosphine is described. This ligand was highly efficient in the ruthenium-catalyzed asymmetric hydrogenation of various aromatic and heteroaromatic ketones.
Key words
paracyclophane - hydrogenation - ruthenium - ketones - P,P-ligands
-
1a
Noyori R. Asymmetric Catalysis in Organic Synthesis Wiley; New York: 1994. -
1b
Ohkuma T.Kitamura M.Noyori R. In Catalytic Asymmetric SynthesisOjima I. Wiley-VCH; Weinheim: 2000. p.1 -
1c
Spindler F.Blaser H.-U. In Transition Metals for Organic Synthesis, 2nd ed. Vol. 2Beller M.Bolm C. Wiley-VCH; Weinheim: 2004. p.113-123 -
1d
Blaser H.-U.Malan C.Pugin B.Spidler F.Steiner H.Studer M. Adv. Synth. Catal. 2003, 345: 103 - 2
Handbook of Enantioselective Catalysis
Vol. 2:
Brunner H.Zettlmeier W. Wiley-VCH; New York: 1993. - 3
Gibson SE.Knight JD. Org. Biomol. Chem. 2003, 1: 1256 - 4
Rossen K.Pye P.Reamer RA.Tsou NN.Volante RP.Reider PJ. J. Am. Chem. Soc. 1997, 119: 6207 - 5
Boulton LT.Lennon IC.McCague R. Org. Biomol. Chem. 2003, 1: 1094 - 6
Pye PJ.Rossen K.Reamer RA.Volante RP.Reider PJ. Tetrahedron Lett. 1998, 39: 4441 - 7
Burk MJ.Hems WP.Herzburg D.Malan C.Zanotti-Gerosa A. Org. Lett. 2000, 2: 4173 - 8
Rossen K.Pye PJ.Maliakal A.Volante RP. J. Org. Chem. 1997, 62: 6462 - 9
Zanotti-Gerosa A.Malan C.Herzburg D. Org. Lett. 2001, 3: 3687 - 10
Dominguez B.Zanotti-Gerosa A.Hems W. Org. Lett. 2004, 6: 1927 - 11 For the preparation of the dibromide, see ref. 6, and for the preparation of the racemic dibromide, see:
Reich HJ.Cram DJ. J. Am. Chem. Soc. 1969, 91: 3527 -
12a
Korff C.Helmchen G. Chem. Commun. 2004, 530 -
12b
Liu D.Tang W.Zhang X. Org. Lett. 2004, 6: 513 -
13a
Ohkuma T.Ooka H.Hashiguchi S.Ikariya T.Noyori R. J. Am. Chem. Soc. 1995, 117: 2675 -
13b
Ohkuma T.Ooka H.Yamakawa M.Ikariya T.Noyori R. J. Am. Chem. Soc. 1995, 117: 10417 -
13c
Doucet H.Ohkuma T.Murata K.Yokozawa T.Kozawa M.Katayama E.England AF.Ikariya T.Noyori R. Angew. Chem. Int. Ed. 1998, 37: 1703 -
14a
Ohkuma T.Koizumi M.Doucet H.Pham T.Kozawa M.Murata K.Katayama E.Yokozawa T.Ikariya T.Noyori R. J. Am. Chem. Soc. 1998, 120: 13529 -
14b
Wu J.Chen H.Kwok W.-H.Guo R.-W.Zhou Z.-Y.Yeung C.-H.Chan ASC. J. Org. Chem. 2002, 67: 7908 -
14c
Cao P.Zhang X. J. Org. Chem. 1999, 64: 2127 -
14d
Ohkuma T.Koizumi M.Yoshida M.Noyori R. Org. Lett. 2000, 2: 1749 -
14e
Noyori R.Ohkuma T. Pure Appl. Chem. 1999, 71: 1493 -
14f
Mikami K.Korenaga T.Terada M.Ohkuma T.Pham T.Noyori R. Angew. Chem. Int. Ed. 1999, 38: 495 - 16
Ponzo VL.Kaufman TS. Tetrahedron Lett. 1995, 36: 9105
References
We used only the two diamines (R,R)-DPEN and (S,S)-DPEN; DPEN = 1,2-diphenylethylenediamine. Complex 6a was prepared by use of the (R,R)-amine, whereas the (S,S)-diamine was used for complex 6b.