A rapid 1H NMR assay for enantiomeric excess of α-substituted aldehydes

被引：28

作者：

Chi, Y ^{[1
]}

Peelen, TJ ^{[1
]}

Gellman, SH ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 16期

关键词：

D O I：

10.1021/ol051174u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] In situ derivatization of a variety of alpha-substituted aldehydes via reaction with chiral amines allows convenient and efficient determination of enantiomeric excess. H-1 NMR analysis of the imine diastereomer ratio can be conducted immediately after the aldehyde and amine have been mixed. The results correlate well with ee values determined by more traditional (and slower) methods. This approach may be broadly applicable to alpha-substituted aldehydes.

引用

页码：3469 / 3472

页数：4

共 26 条

[1] Berkessel A, 2002, EUR J ORG CHEM, V2002, P2800, DOI 10.1002/1099-0690(200208)2002:16<2800::AID-EJOC2800>3.0.CO
[2] 2-4
[3] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors
Betancort, JM
Barbas, CF
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3737 - 3740
[4] Böhm A, 2000, HELV CHIM ACTA, V83, P3262, DOI 10.1002/1522-2675(20001220)83:12<3262::AID-HLCA3262>3.0.CO
[5] 2-P
[6] Protonated chiral catalysts: Versatile tools for asymmetric synthesis
Bolm, C
Rantanen, T
Schiffers, I
Zani, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) : 1758 - 1763
[7] Addition vs abstraction reactions of the methyl radical with nitrones, alkenes, aldehydes, and imines
Boyd, SL
Boyd, RJ
[J]. JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (29) : 7096 - 7105
[8] The direct amino acid-catalyzed asymmetric incorporation of molecular oxygen to organic compounds
Córdova, A
Sundén, H
Engqvist, M
Ibrahem, I
Casas, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) : 8914 - 8915
[9] An enantioselective NMR shift reagent for cationic aromatics
Dignam, CF
Richards, CJ
Zopf, JJ
Wacker, LS
Wenzel, TJ
[J]. ORGANIC LETTERS, 2005, 7 (09) : 1773 - 1776
[10] Catalytic asymmetric intramolecular Michael reaction of aldehydes
Fonseca, MTH
List, B
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) : 3958 - 3960

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