Abstract
New terdentate facially binding ligands based on the 2-pyridinyl-α-ethanol skeleton
were prepared as the racemates. Reaction with the enantiomerically pure (-)-(1S,4R)-camphanoyl chloride gave diastereomeric camphanic esters. The pure diastereomers
were accessible by separating the diastereomeric esters with medium-pressure silica
gel chromatography or fractional crystallization. X-ray structure analysis of the
pure camphanic esters established the absolute configurations of the 2-pyridinyl-α-alcohols.
The enantiomerically pure alcohols were obtained after saponification of the diastereomerically
pure esters.
Key words
facial coordination - terdentate ligands - chiral 2-pyridinyl-α-alcohols - absolute
configuration
References
<A NAME="RZ04601SS-1">1</A> Part 137:
Brunner H.
Kagan HB.
Kreutzer G.
Tetrahedron: Asymmetry
2001,
12:
497
<A NAME="RZ04601SS-2">2</A>
X-ray structure analyses.
<A NAME="RZ04601SS-3">3</A>
Horner L.
Siegel H.
Büthe H.
Angew. Chem. Int. Ed. Engl.
1968,
9:
942
<A NAME="RZ04601SS-4">4</A>
Knowles WS.
Sabacky MJ.
J. Chem. Soc., Chem. Commun.
1968,
1445
<A NAME="RZ04601SS-5">5</A>
Brunner H.
Zettlmeier W.
Handbook of Enantioselective Catalysis
Vol. I and II:
VCH;
Weinheim:
1993.
<A NAME="RZ04601SS-6">6</A>
Brunner H.
Angew. Chem. Int. Ed.
1999,
38:
1194
<A NAME="RZ04601SS-7">7</A>
Mauleón D.
Pujol MD.
Minguillón C.
Miquel J.
J. Heterocycl. Chem.
1989,
26:
693
<A NAME="RZ04601SS-8">8</A>
Orrenius C.
Mattson A.
Norin T.
Öhrner N.
Hult K.
Tetrahedron: Asymmetry
1994,
5:
3041
<A NAME="RZ04601SS-9">9</A>
Thurkauf A.
Mattson MV.
Richardson S.
Mirsadeghi S.
Ornstein PL.
Harrison EA.
Rice KC.
Jacobson AE.
Monn JA.
J. Med. Chem.
1992,
35:
1323
<A NAME="RZ04601SS-10">10</A>
Crystallographic data (excluding structure factors)for the structures in this paper
have been deposited with the Cambridge Crystallographic Data Centre as supplementary
publication nos. CCDC 162515 [for (±)-3], CCDC 162518 [for (±)-5], CCDC 162514 [for(diphenylphosphanyl)methyl-2-pyridinylketone], CCDC 162512 [for(phenylsulfanyl)methyl-2-pyridinylketone],
CCDC 162513 [for (2S,4S)-2-(2-pyridinyl)-4-carboethoxy-1,3-thiazolidine: BESTHIA], CCDC 162516 [for (S)-(-)-9], CCDC 162520 [for (R)-(-)-11], CCDC 162517 [for (S)-(+)-12] and CCDC 162519 [for (R)-(-)-13]. Copies of the data can be obtained, free of charge, on application to CCDC, 12
Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
<A NAME="RZ04601SS-11">11</A>
MijoloviĘ D.
Ph. D. Thesis
Universität Regensburg;
Germany:
2001.
<A NAME="RZ04601SS-12">12</A>
Sharpless BK.
Amberg W.
Bennani YL.
Crispino GA.
Hartung J.
Jeong K.
Kwong H.
Morikawa K.
Wang Z.
Xu D.
Zhang X.
J. Org. Chem.
1992,
57:
2768
<A NAME="RZ04601SS-13">13</A>
Genzel Y.
Archelas A.
Broxterman QB.
Schulze B.
Furstoss R.
Tetrahedron: Asymmetry
2000,
11:
3041
<A NAME="RZ04601SS-14">14</A>
Palucki M.
McCormick GJ.
Jacobsen EN.
Tetrahedron Lett.
1995,
36:
5457
<A NAME="RZ04601SS-15">15</A>
Brunner H.
Kürzinger A.
J. Organomet. Chem.
1988,
346:
413
<A NAME="RZ04601SS-16">16</A>
Kitamura M.
Ohkuma T.
Inoue S.
Sayo N.
Kumobayashi H.
Akutagawa S.
Ohta T.
Takaya H.
Noyori R.
J. Am. Chem. Soc.
1988,
110:
629
<A NAME="RZ04601SS-17">17</A>
Kitamura M.
Tokunaga M.
Ohkuma T.
Noyori R.
Org. Synth.
1998,
Coll. Vol. IX:
589
<A NAME="RZ04601SS-18">18</A>
Ishizaki M.
Fujita K.
Shimamoto M.
Hoshino O.
Tetrahedron: Asymmetry
1994,
5:
411
<A NAME="RZ04601SS-19">19</A>
Gerlach H.
Kappes D.
Boeckman RK.
Maw GN.
Org. Synth.
1998,
Coll. Vol. IX:
151
<A NAME="RZ04601SS-20">20</A>
Bolm C.
Ewald M.
Felder M.
Schlinghoff G.
Chem. Ber.
1992,
125:
1169