3-Substituted BINOL schiff bases and their reductive products for catalytic asymmetric addition of diethylzinc to aldehydes

Chirality

Volumn 20, Issue 7, 2008, Pages 828-832

  Liu, Bing ^a,b   Dong, Zhi Bing ^a   Fang, Cao ^a   Song, Hai Bin ^a   Li, Jin Shan ^a  

^a NANKAI UNIVERSITY   (China)

^b TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Aldehyde; Asymmetric addition; BINOL; Schiff base; Titanium

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; DIETHYLZINC; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SCHIFF BASE; TITANIUM; TITANIUM TETRAISOPROPOXIDE; ALDEHYDE; BINOL, NAPHTHOL; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LIGAND; NAPHTHOL DERIVATIVE; ORGANOMETALLIC COMPOUND;

ADDITION REACTION; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; ENANTIOSELECTIVITY; OPTICAL ROTATION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

ALDEHYDES; INDICATORS AND REAGENTS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NAPHTHOLS; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; SCHIFF BASES; STEREOISOMERISM;

EID: 45849142569     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20559     Document Type: Article

References (32)

1. Noyori R. Asymmetric catalysis in organic synthesis. New York: Wiley; 1994. Chapter 5.
2. Noyori R, Kitamura M. Enantioselective addition of organometallic reagents to carbonyl compound: chirality transfermultiplicationand amplification. Angew Chem Int Ed Engl 1991;30:49-69.
3. Soai K, Niwa S. Enantioselective addition of organozinc reagents to aldehydes. Chem Rev 1992;92:833-856.
4. Paleo MR, Cabeza I, Sardina FJ. Enantioselective addition of diethylzinc to aldehydes catalyzed by N-(9-Phenylfluoren-9-yr) b-amino alcohols. J Org Chem 2000;65:2108-2113.
5. Hanyu N, Mino T, Sakamoto M, Fujita T. Facile synthesis of amino bicyclo[2.2.1]heptyl alcohol and its application for enantioselective additions of diethylzinc to aldehydes. Tetrahedron Lett 2000;41:4587-4590.
6. Hanyu N, Aoki T, Mino T, Sakamoto M, Fujita T. Enantioselective addition of diethylzinc to aldehydes catalyzed by optically active 1,4-aminoalcohols. Tetrahedron: Asymmetry 2000;11:2971-2979.
7. 2 to aromatic aldehydes. Tetrahedron: Asymmetry 2001;12:1235-1239.
8. Priego J, Mancheno OG, Cabrera S, Carretero JC. 2-Aminosubstituted 1-sulfinylferrocenes as chiral ligands in the addition of diethylzinc to aromatic aldehydes. J Org Chem 2002;67:1346-1353.
9. Fontes M, Verdaguer X, Sola L, Pericas M, Riera A. 2-Piperidino-1,1,2- triphenylethanol: a highly effective catalyst for the enantioselective arylation of aldehydes. J Org Chem 2004;69:2532-2543.
10. Heckel A, Seebach D. Immobilization of TADDOL with a high degree of loading on porous silica gel and first applications in enantioselective catalysis. Angew Chem Int Ed 2000;39:163-165.
11. 2-symmetric chiral bis(oxazoline) ligands and their application in the enantioselective addition of diethylzinc to aldehydes. Tetrahedron: Asymmetry 2004;15:119-126.
12. 2 to carbonyl compounds. Org Lett 2001;3:4259-4262.
13. Niwa S, Soai K. Asymmetric synthesis using chiral piperazines. III. Enantioselective addition of dialkylzincs to aryl aldehydes catalysed by chiral piperazines. J Chem Soc Perkin Trans 1 1991;28:2717-2720.
14. Conti S, Falorni M, Giacomelli G, Soccolini F. Chiral ligands containing heteroatoms. 10. 1-(2-pyridyl)alkylamines as chiral catalysts in the addition of diethylzinc to aldehydes: temperature dependence on the enantioselectivity. Tetrahedron 1992;48:8993-9000.
15. Pu L. 1,1′-Binaphthyl dimers, oligomers, and polymers: molecular recognition, asymmetric catalysis, and new materials. Chem Rev 1998;98:2405-2494.
16. Chen Y, Yekta S, Yudin AK. Modified BINOL ligands in asymmetric catalysis. Chem Rev 2003;103:3155-3212.
17. Koîcovskú P, Vyskoîcil S, Smrîcina M. Non-symmetrically substituted 1,1′-Binaphthyls in enantioselective catalysis. Chem Rev 2003;103: 3213-3245.
18. Brunel JM. BINOL: a versatile chiral reagent. Chem Rev 2005;105: 857-897.
19. Mori M, Nakai T. Asymmetric catalytic alkylation of aldehydes with diethylzinc using a chiral binaphthol-titanium complex. Tetrahedron Lett 1997;38:6233-6236.
20. Zhang FY, Yip CW, Cao R, Chan ASC. Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by Ti(BINOL) complex. Tetrahedron: Asymmetry 1997;8:585-589.
21. 4-BINOL ligand and its application to titanium-catalyzed enantioselective addition of diethylzinc to aldehydes. Tetrahedron: Asymmetry 2000;11:4321-4327.
22. Zhang FY, Chan ASC. Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by titanium-5,5′,6,6′,7,7′,8,8′- octahydro-1,1′-bi-2-naphthol complex. Tetrahedron: Asymmetry 1997;8:3651-3655.
23. Matsui K, Takizawa S, Sasai H. Bifunctional organocatalysts for enantioselective aza-Morita-Baylis-Hillman reaction. J Am Chem Soc 2005; 127:3680-3681.
24. Matsui K, Tanaka K, Horii A, Takizawa S, Sasai H. Conformational lock in a Bransted acid-Lewis base organocatalyst for the aza-Morita-Baylis-Hillman reaction. Tetrahedron: Asymmetry 2006;17:578-583.
25. 2-symmetric, chirally economical, and readily tunable linked-binols: design and application in a direct catalytic asymmetric Mannich-Type reaction. Angew Chem Int Ed 2005;44:3470-3474.
26. Ihori Y, Yamashita Y, Ishitani H, Kobayashi S. Chiral zirconium catalysts using multidentate BINOL derivatives for catalytic enantioselective Mannich-Type reactions; ligand optimization and approaches to elucidation of the catalyst structure. J Am Chem Soc 2005;127:15528-15535.
27. Harada T, Kanda K. Enantioselective alkylation of aldehydes catalyzed by a highly active titanium complex of 3-substituted unsymmetric BINOL. Org Lett 2006;8:3817-3819.
28. Guo QS, Liu B, Lu YN, Jiang FY, Song HB, Li JS. Synthesis of 3 or 3,3′-substituted BINOL ligands and their application in the asymmetric addition of diethylzinc to aromatic aldehydes. Tetrahedron: Asymmetry 2005;16:3667-3671.
29. Guo QS, Lu YN, Liu B, Xiao J, Li JS. A facile synthesis of 3 or 3,3′-substituted binaphthols and their applications in the asymmetric addition of diethylzinc to aldehydes. J Organomet Chem 2006;691:1282-1287.
30. Lin J, Rajaram AR, Pu L. Enantioselective fluorescent recognition of chiral acids by 3- and 3,3′-aminomethyl substituted BINOLs. Tetrahe dron 2004;60:11277-11281.
31. Dave R, Sasaki NA. Synthesis of chiral C/N-functionalized morpholine alcohols: study of their catalytic ability as ligand in asymmetric diethylzinc addition to aldehyde. Tetrahedron: Asymmetry 2006;17:388-401.
32. Dai WM, Zhu HJ, Hao XJ. Chiral ligands derived from abrine. VI. Importance of a bulky N-alkyl group in indole-containing chiral β-tertiary amino alcohols for controlling enantioselectivity in addition of diethylzinc toward aldehydes. Tetrahedron: Asymmetry 2000;11:2315-2337.