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
References
<A NAME="RT13507SS-1A">1a </A>
Noyori R.
Asymmetric Catalysis in Organic Synthesis
Wiley;
New York:
1994.
<A NAME="RT13507SS-1B">1b </A>
Ohkuma T.
Kitamura M.
Noyori R. In Catalytic Asymmetric Synthesis
Ojima I.
Wiley-VCH;
Weinheim:
2000.
p.1
<A NAME="RT13507SS-1C">1c </A>
Spindler F.
Blaser H.-U. In
Transition Metals for Organic Synthesis, 2nd ed. Vol. 2
Beller M.
Bolm C.
Wiley-VCH;
Weinheim:
2004.
p.113-123
<A NAME="RT13507SS-1D">1d </A>
Blaser H.-U.
Malan C.
Pugin B.
Spidler F.
Steiner H.
Studer M.
Adv. Synth. Catal.
2003,
345:
103
<A NAME="RT13507SS-2">2 </A>
Handbook of Enantioselective Catalysis
Vol. 2:
Brunner H.
Zettlmeier W.
Wiley-VCH;
New York:
1993.
<A NAME="RT13507SS-3">3 </A>
Gibson SE.
Knight JD.
Org. Biomol. Chem.
2003,
1:
1256
<A NAME="RT13507SS-4">4 </A>
Rossen K.
Pye P.
Reamer RA.
Tsou NN.
Volante RP.
Reider PJ.
J. Am. Chem. Soc.
1997,
119:
6207
<A NAME="RT13507SS-5">5 </A>
Boulton LT.
Lennon IC.
McCague R.
Org. Biomol. Chem.
2003,
1:
1094
<A NAME="RT13507SS-6">6 </A>
Pye PJ.
Rossen K.
Reamer RA.
Volante RP.
Reider PJ.
Tetrahedron Lett.
1998,
39:
4441
<A NAME="RT13507SS-7">7 </A>
Burk MJ.
Hems WP.
Herzburg D.
Malan C.
Zanotti-Gerosa A.
Org. Lett.
2000,
2:
4173
<A NAME="RT13507SS-8">8 </A>
Rossen K.
Pye PJ.
Maliakal A.
Volante RP.
J. Org. Chem.
1997,
62:
6462
<A NAME="RT13507SS-9">9 </A>
Zanotti-Gerosa A.
Malan C.
Herzburg D.
Org. Lett.
2001,
3:
3687
<A NAME="RT13507SS-10">10 </A>
Dominguez B.
Zanotti-Gerosa A.
Hems W.
Org. Lett.
2004,
6:
1927
<A NAME="RT13507SS-11">11 </A> 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
<A NAME="RT13507SS-12A">12a </A>
Korff C.
Helmchen G.
Chem. Commun.
2004,
530
<A NAME="RT13507SS-12B">12b </A>
Liu D.
Tang W.
Zhang X.
Org. Lett.
2004,
6:
513
<A NAME="RT13507SS-13A">13a </A>
Ohkuma T.
Ooka H.
Hashiguchi S.
Ikariya T.
Noyori R.
J. Am. Chem. Soc.
1995,
117:
2675
<A NAME="RT13507SS-13B">13b </A>
Ohkuma T.
Ooka H.
Yamakawa M.
Ikariya T.
Noyori R.
J. Am. Chem. Soc.
1995,
117:
10417
<A NAME="RT13507SS-13C">13c </A>
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
<A NAME="RT13507SS-14A">14a </A>
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
<A NAME="RT13507SS-14B">14b </A>
Wu J.
Chen H.
Kwok W.-H.
Guo R.-W.
Zhou Z.-Y.
Yeung C.-H.
Chan ASC.
J. Org. Chem.
2002,
67:
7908
<A NAME="RT13507SS-14C">14c </A>
Cao P.
Zhang X.
J. Org. Chem.
1999,
64:
2127
<A NAME="RT13507SS-14D">14d </A>
Ohkuma T.
Koizumi M.
Yoshida M.
Noyori R.
Org. Lett.
2000,
2:
1749
<A NAME="RT13507SS-14E">14e </A>
Noyori R.
Ohkuma T.
Pure Appl. Chem.
1999,
71:
1493
<A NAME="RT13507SS-14F">14f </A>
Mikami K.
Korenaga T.
Terada M.
Ohkuma T.
Pham T.
Noyori R.
Angew. Chem. Int. Ed.
1999,
38:
495
<A NAME="RT13507SS-15">15 </A>
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 .
<A NAME="RT13507SS-16">16 </A>
Ponzo VL.
Kaufman TS.
Tetrahedron Lett.
1995,
36:
9105