Chiral ligands derived from abrine. Part 6: Importance of a bulky N-alkyl group in indole-containing chiral beta-tertiary amino alcohols for controlling enantioselectivity in addition of diethylzinc toward aldehydes
Dai, WM; Zhu, HJ; Hao, XJ
2000-06-16
Source PublicationTETRAHEDRON-ASYMMETRY
ISSN0957-4166
Volume11Issue:11Pages:2315-2337
AbstractA number of chiral beta-amino alcohols possessing a 3-indolylmethyl group have been synthesized from the alkaloid (S)-abrine and elucidated for potency in the catalytic enantioselective ethylation of PhCHO with Et2Zn. In general, the secondary amines 15a-d bearing a dialkylhydroxymethyl group induced (R)-1-phenyl-1-propanol, whereas 15e-g and 18 bearing a diarylhydroxymethyl group favored the (S)-enantiomer. In contrast, the beta-tertiary amino alcohols 20b d and 21 produced (R)-1-phenyl-1-propanol. regardless of the substituents at the carbon bearing the hydroxy group. Enantiomeric excess of 87.5% was obtained for (R)-1-phenyl-1-propanol using ligand 21 as the promoter. Eleven substituted benzaldehydes and naphth-aldehydes were examined for enantioselective ethylation by using 21 and the chiral alcohols were obtained in 93-97% ee, except for o-BrC6H4CHO and p-Me2NC6H4CHO. Excellent enantioselectivity was also observed in the ethylation of cyclohexanecarboxaldehyde (94.8% ee) and 2-thiophenecarboxaldehyde (94.9% ee) by using catalytic 21. The anti 5/4/4-fused tricyclic TS I was proposed to rationalize the asymmetric induction. The diethylhydroxymethyl and N-2-t-butylethyl groups are believed to enforce the preference for the anti-TS(R) I and it results in high enantioselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.
KeywordAsymmetric Autocatalytic Reaction Aromatic-aldehydes Dialkylzinc Reagents Organozinc Reagents Enantiomeric Excess Organometallic Reagents Ephedrine Derivatives Aliphatic-aldehydes Aryl Aldehydes Catalysts
Subject AreaChemistry, Inorganic & Nuclear ; Chemistry, Organic ; Chemistry, Physical
Indexed BySCI ; IC
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Inorganic & Nuclear ; Chemistry, Organic ; Chemistry, Physical
WOS IDWOS:000087888600011
Citation statistics
Cited Times:71[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/4350
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, Kunming 650204, Yunnan, Peoples R China
Recommended Citation
GB/T 7714
Dai, WM,Zhu, HJ,Hao, XJ. Chiral ligands derived from abrine. Part 6: Importance of a bulky N-alkyl group in indole-containing chiral beta-tertiary amino alcohols for controlling enantioselectivity in addition of diethylzinc toward aldehydes[J]. TETRAHEDRON-ASYMMETRY,2000,11(11):2315-2337.
APA Dai, WM,Zhu, HJ,&Hao, XJ.(2000).Chiral ligands derived from abrine. Part 6: Importance of a bulky N-alkyl group in indole-containing chiral beta-tertiary amino alcohols for controlling enantioselectivity in addition of diethylzinc toward aldehydes.TETRAHEDRON-ASYMMETRY,11(11),2315-2337.
MLA Dai, WM,et al."Chiral ligands derived from abrine. Part 6: Importance of a bulky N-alkyl group in indole-containing chiral beta-tertiary amino alcohols for controlling enantioselectivity in addition of diethylzinc toward aldehydes".TETRAHEDRON-ASYMMETRY 11.11(2000):2315-2337.
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