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手性羟基酸或氨基酸及其衍生物催化二乙基锌与苯甲醛对映选择性加成反应 被引量：2

ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO BENZALDEHYDE CATALYSED BY CHIRAL HYDROXYL ACIDS OR AMINO ACIDS AND THEIR DERIVATIVES
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摘要 L 乳酸、(S) 扁桃酸和L 缬氨酸以及它们的某些衍生物在反应体系中与Ti(OPr i) 4作用 ,生成的配合物对二乙基锌与苯甲醛的对映选择性加成反应均有催化作用 ,化学产率为6 1.2 %～ 91.5 % .在用扁桃酸做催化剂时 ,产物的光学产率较高 ,达到 5 8% . L lactic acid, ( S ) mandelic acid, L valine and their derivatives mixed with titanium tetraisoproxide in situ can catalyze the addition of diethylzinc to benzaldehyde in good chemical yields(61.2%～91.5%). The Y ee of the product is up to 58% when ( S ) mandelic acid is used as catalyst.
作者 张站斌 尹承烈
机构地区 北京师范大学化学系
出处 《北京师范大学学报（自然科学版）》 CAS CSCD 北大核心 2002年第2期222-225,共4页 Journal of Beijing Normal University(Natural Science)
关键词 手性 羟基酸 氨基酸 衍生物 二乙基锌 苯甲醛 选择性加成反应 L-乳酸 (S)-扁桃酸 diethylzinc enantioselective addition L lactic acid ( S ) mandelic acid L valine
分类号 O627.23 [理学—有机化学]
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参考文献7

  • 1[1]Noyori R,Kitamura M.Enantioselective addition of organicmetallic reagents to carbonyl compounds: chirality transfer,multiplication and amplification[J].Angew Chem Int Ed Engl,1991,30:49
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  • 3[3]Zhang Fuyao,Chan A S C.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[J].Tetrahydron: Asymmetry,1997,8(21):3651
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同被引文献17

  • 1周忠强,郭娅静,武利华.氨基醇催化苯乙酮的不对称还原反应[J].中南民族大学学报（自然科学版）,2007,26(2):11-14. 被引量：1
  • 2周忠强,罗冬冬.不对称催化烷基化反应中配体研究进展[J].广州化学,2005,30(3):55-61. 被引量：6
  • 3NOYORI R. Asymmetric catalysis in organic synthesis [ M ]. New York :John Wiley & Sons, 1994:255-297.
  • 4SOAI K, NIWA S. Enantioselective addition of organozinc reagents to aldehydes [J]. Chem. Rev, 1992,92 (5) : 833- 856.
  • 5BLAY G, FERNANDEZ I, MARCO-ALEIXANDRE A, et al. Chiral bis(amino alcohol)oxalamides as ligands for asymmetric catalysis.Ti( Ⅳ ) catalyzed enantioselective addition of diethylzinc to aldehydes [ J] . Tetrahedron Asymmetry, 2005,16 (6) :1 207-1 213.
  • 6韩广甸，范如霖，李述文．有机制备化学手册(下卷)[M]．第一版．北京：石油化学工业出版社，1978：128-131．
  • 7BARTLETT P D, KNOX L H. D, L- Camphorsulfonyl chloride [M]//Organic Synthesis. Volume 45. New York:John Wiley & Sons, 1965 : 14-16.
  • 8BARTLETr P D, KNOX L H. D, L- Ketopinic acid [ M. ]//Organic Synthesis. Collective Volume 5. New York : John Wiley & Sons,1973:689-691.
  • 9HWANG C D, UANG B J. Enantioselective addition of diethylzinc to aldehydes induced by a new chiral Ti( Ⅳ ) catalyst[ J]. Tetrahedron Asymmetry, 1998,9(22) : 3 979-3 984.
  • 10Soai K, Niwa S. Enantioselective Addition of Organozinc Reagents to Aldehydes [J]. Chemical Reviews, 1992,92 (5) : 833-856.

引证文献2

北京师范大学学报（自然科学版）
2002年 第2期

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