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Synthesis 2007(16): 2461-2470
DOI: 10.1055/s-2007-983787
DOI: 10.1055/s-2007-983787
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis and Applications of 3-[6-(Hydroxymethyl)pyridin-2-yl]-1,1′-bi-2-naphthols or 3,3′-Bis[6-(hydroxymethyl)pyridin-2-yl]-1,1′-bi-2-naphthols
Weitere Informationen
Received
9 January 2007
Publikationsdatum:
12. Juli 2007 (online)
Publikationsverlauf
Publikationsdatum:
12. Juli 2007 (online)
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Abstract
A series of new 1,1′-bi-2-naphthol (BINOL) derived ligands, 3-[6-(hydroxymethyl)pyridin-2-yl]-BINOLs or 3,3′-bis[6-(hydroxymethyl)pyridin-2-yl]-BINOLs, bearing one or two chiral pyridinylmethanols attached to a binaphthyl skeleton, have been synthesized using the Suzuki cross-coupling reaction. The resulting compounds have been used as ligands in the enantioselective addition of diethylzinc to aldehydes; the products were obtained with up to 96% ee.
Key word
pyridin-2-ylmethanol - BINOL - Suzuki cross-coupling reaction - asymmetric catalysis
- 1
Chen Y.Yekta S.Yudin AK. Chem. Rev. 2003, 103: 3155 - 2
Kočovský P.Vyskočil S.Smrčina M. Chem. Rev. 2003, 103: 3213 -
3a
Luo Z.Liu Q.Gong L.Cui X.Mi A.Jiang Y. Angew. Chem. Int. Ed. 2002, 41: 4532 -
3b
Luo Z.Liu Q.Gong L.Cui X.Mi A.Jiang Y. Chem. Commun. 2002, 914 -
3c
Somei H.Asano Y.Yoshida T.Takizawa S.Yamataka H.Sasai H. Tetrahedron Lett. 2004, 45: 1841 -
3d
Jeong Y.-C.Choi S.Hwang YD.Ahn K.-H. Tetrahedron Lett. 2004, 45: 9249 -
3e
Kodama H.Ito J.Hori K.Ohta T.Furukawa I. J. Organomet. Chem. 2000, 603: 6 -
4a
Kwong H.-L.Lee W.-S. Tetrahedron: Asymmetry 1999, 10: 3791 -
4b
Kühn FE.Santos AM.Lopes AD.Gonçalves IS.Rodríguez-Borges JE.Pillinger M.Romão CC. J. Organomet. Chem. 2001, 621: 207 -
4c
Herrmann WA.Haider JJ.Fridgen J.Lobmaier GM.Spiegler M. J. Organomet. Chem. 2000, 603: 69 -
5a
Bai X.-L.Liu X.-D.Wang M.Kang C.-Q.Gao L.-X. Synthesis 2005, 458 -
5b
Jin R.-Z.Bian Z.Kang C.-Q.Guo H.-Q.Gao L.-X. Synth. Commun. 2005, 35: 1897 - 6
Lecomte V.Stéphan E.Bideau FB.Jaouen G. Tetrahedron 2003, 59: 2169 - For reviews, see:
-
8a
Soai K.Niwa S. Chem. Rev. 1992, 92: 833 -
8b
Noyori R.Kitamura M. Angew. Chem., Int. Ed. Engl. 1991, 30: 49 -
8c
Pu L.Yu H.-B. Chem. Rev. 2001, 101: 757 - 9
Zhang F.-Y.Yip C.-W.Cao R.Chan ASC. Tetrahedron: Asymmetry 1997, 8: 585
References
The product with one MOM removed was determined by 1H NMR.