期刊文献+

新手性磺酰胺醇催化二乙基锌对苯甲醛的不对称加成反应

Enantioselective addition of diethylzinc to benzaldehyde with new chiral sulfonamide alcohols as ligands
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摘要 由天然樟脑和(L)-苯丙氨酸合成了4个新的手性磺酰胺醇,并对其在二乙基锌对苯甲醛的不对称加成中的催化性能进行了研究。这4个手性磺酰胺醇表现出中等程度的催化活性和较差的不对称诱导作用。 Four new chiral sulfonamide alcohols were synthesized from camphor and L-phenylalanine and their application to the enantioselective addition of diethylzinc to benzaldehyde was described. Sulfonamide alcohols were found to have moderate catalytic activity and weak asymmetric induction during the addition of diethylzinc to benzaldehyde.
作者 周忠强
出处 《化学试剂》 CAS CSCD 北大核心 2007年第3期135-137,140,共4页 Chemical Reagents
基金 湖北省自然科学基金资助项目(2003ABA070)
关键词 磺酰胺醇 二乙基锌 加成 sulfonamide alcohol diethylzinc addition
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参考文献10

  • 1NOYORI R. Asymmetric catalysis in organic synthesis [ M ]. New York : John Wiley & Sons, 1994 : 255-297.
  • 2SOAI K, NIWA S. Enantioselective addition of organozinc reagents to aldehydes [ J ]. Chem. Rev, 1992,92 ( 5 ) : 833-856.
  • 3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
  • 4周忠强,郭娅静.新型手性羟基磺酰胺催化二乙基锌对芳香醛的不对称加成反应[J].现代化工,2005,25(6):37-39. 被引量:4
  • 5BARTLETr P D, KNOX L H. D, L-Camphorsulfonyl chloride [ M]// Organic Synthesis. Volume 45. New York : John Wiley & Sons, 1965 : 14-16.
  • 6思洋,刘乐乐,张廓,姜萍萍.氨基酸甲乙酯的合成及纯化[J].内蒙古医学院学报,2005,27(1):33-34. 被引量:18
  • 7DA Chao-shan, HAN Zhi-jian, NI Ming, et al. A convenient synthesis of piperidine-based β-amino alcohols from L-Phe and highly enantioselective addition of diethyl zinc to aldehydes [ J ]. Tetrahedron : Asymmetry,2003,14(6) : 659-665.
  • 8HWANG Chyuan-der, UANG Biing-jiun. Enantioselective addition of diethylzinc to aldehydes induced by a new chiral Ti ( Ⅳ ) catalyst [ J ]. Tetrahedron : Asymmetry, 1998,9 ( 22 ) : 3 979-3 984.
  • 9DAI Wei-min, ZHU Hua-jie, HAO Xiao-jiang. Chiral ligands derived from abrine, part 6: importance of a bulky N-alkyl group in indole-containing chiral β-tertiary amino alcohols for controlling enantioselectivity in addition of diethylzinc toward aldehydes[J]. Tetrahedron : Asymmetry ,2000,11(11) :2 315- 2 337.
  • 10YOU Jing-song, SHAO Ming-yuan, GAU Han-mou. Enantioselective addition of diethylzinc to aldehydes catalyzed by titanium( Ⅳ ) complexes of N-sulfonylated amino alcohols with two stereogenic centers [ J ]. Tetrahedron : Asymmetry, 2001,12(21) :2 971-2 975.

二级参考文献55

  • 1Brenner M, Hely HW. Preparation of α-amino acid esters by alcoholysis of the methylesters [J]. Chim Acta, 1953;36:1109-1114.
  • 2Knollmuller M, Ferencic M, Gartner P. Enantioselective addition of organometallics to aldehydes using camphor derived chiral 1,4-aminoalcohols as ligands [J]. Tetrahedron Asymmetry, 1999, 10:3969-3975.
  • 3Nakamura Y, Takeuchi S, Okumura K, et al. Enantioselective addition of diethylzinc to aldehydes catalyzed by fluorous β-aminoalcohols [J]. Tetrahedron, 2001, 57: 5565-5571.
  • 4Kawanami Y, Mitsuie T, Miki M, et al. New chiral ligands derived from (S)-leucine for the enantioselective addition of diethylzinc to aldehydes [J]. Tetrahedron, 2000, 56: 175-178.
  • 5Takahiko O, Satoshi U, Yasuhiro K. Enantioselective addition of diethylzinc to aldehydes catalyzed by chiral amino alcohols, substituent effect and nonlinear effect [J]. Tetrahedron, 2001, 57: 4825-4829.
  • 6Da C, Hah Z, Ni M, et al. A convenient synthesis of piperidine-based -amino alcohols from L-Phe and highly enantioselective addition of diethyl zinc to aldehydes [J]. Tetrahedron Asymmetry, 2003, 14: 659-665.
  • 7Wolf C, Francis C J, Hawes P A, et al. Enantioselective alkylation of aldehydes promoted by (S)-tyrosine-derived β-amino alcohols [J]. Tetrahedron Asymmetry, 2002, 13: 1733-1741.
  • 8Dai W M, Zhua H J, Hao X J. Chiral ligands derived from abrine, part 6: importance of a bulky N-alkyl group in indole-containing chiral β-tertiary amino alcohols for controlling enantioselectivity in addition of diethylzinc toward aldehydes [J]. Tetrahedron Asymmetry, 2000, 11: 2315-2337.
  • 9Superchi S, Mecca T, Giorgio E, et al. 1,1-Binaphthylazepine-based ligands for asymmetric catalysis. Part 2:New aminoalcohols as chiral ligands in the enantioselective addition of ZnEt2 to aromatic aldehydes [J].Tetrahedron Asymmetry, 2001, 12: 1235-1239.
  • 10Qian C T, Gao F F, Sun J. First application of amino-TADDOL derivatives in enantioselective addition of diethylzinc to aryl aldehydes: effect of substituents on the nitrogen atom [J]. Tetrahedron Asymmetry, 2000, 11:1733-1740.

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