Highly enantioselective reduction with novel, bridged NADH models

N. Kanomata; T. Nakata

doi:10.1002/anie.199712071

Highly enantioselective reduction with novel, bridged NADH models

N. Kanomata^*, T. Nakata

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

82 Citations (Scopus)

Abstract

Biomimetic reduction of benzoylformate to mandelate with 97-99% ee was achieved with the diastereomeric, bridged NADH models (S.S)-1 and (R.S)-1. The oligomethylene bridge acts as an 'enzyme wall' and hinders the approach of the substrate from one side of the dihydropyridine ring. Isomers 1 were synthesized from the corresponding bridged nicotinate precursor, which was prepared by the reaction of formyl-substituted (vinylimino)phosphorane with methyl propiolate.

Original language	English
Pages (from-to)	1207-1211
Number of pages	5
Journal	Angewandte Chemie - International Edition in English
Volume	36
Issue number	11
DOIs	https://doi.org/10.1002/anie.199712071
Publication status	Published - 1997 Jan 1
Externally published	Yes

Keywords

Asymmetric synthesis
Macrocycles
NADH model compounds
Pyridinophanes

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.199712071

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abstract = "Biomimetic reduction of benzoylformate to mandelate with 97-99% ee was achieved with the diastereomeric, bridged NADH models (S.S)-1 and (R.S)-1. The oligomethylene bridge acts as an 'enzyme wall' and hinders the approach of the substrate from one side of the dihydropyridine ring. Isomers 1 were synthesized from the corresponding bridged nicotinate precursor, which was prepared by the reaction of formyl-substituted (vinylimino)phosphorane with methyl propiolate.",

keywords = "Asymmetric synthesis, Macrocycles, NADH model compounds, Pyridinophanes",

author = "N. Kanomata and T. Nakata",

year = "1997",

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doi = "10.1002/anie.199712071",

language = "English",

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T1 - Highly enantioselective reduction with novel, bridged NADH models

AU - Kanomata, N.

AU - Nakata, T.

PY - 1997/1/1

Y1 - 1997/1/1

N2 - Biomimetic reduction of benzoylformate to mandelate with 97-99% ee was achieved with the diastereomeric, bridged NADH models (S.S)-1 and (R.S)-1. The oligomethylene bridge acts as an 'enzyme wall' and hinders the approach of the substrate from one side of the dihydropyridine ring. Isomers 1 were synthesized from the corresponding bridged nicotinate precursor, which was prepared by the reaction of formyl-substituted (vinylimino)phosphorane with methyl propiolate.

AB - Biomimetic reduction of benzoylformate to mandelate with 97-99% ee was achieved with the diastereomeric, bridged NADH models (S.S)-1 and (R.S)-1. The oligomethylene bridge acts as an 'enzyme wall' and hinders the approach of the substrate from one side of the dihydropyridine ring. Isomers 1 were synthesized from the corresponding bridged nicotinate precursor, which was prepared by the reaction of formyl-substituted (vinylimino)phosphorane with methyl propiolate.

KW - Asymmetric synthesis

KW - Macrocycles

KW - NADH model compounds

KW - Pyridinophanes

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DO - 10.1002/anie.199712071

M3 - Article

AN - SCOPUS:0030739041

SN - 1433-7851

VL - 36

SP - 1207

EP - 1211

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 11

ER -

Highly enantioselective reduction with novel, bridged NADH models

Abstract

Keywords

ASJC Scopus subject areas

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