Designed ligands as probes for the catalytic binding mode in Mo-catalyzed asymmetric allylic alkylation

Barry M. Trost; Kalindi Dogra; Iwao Hachiya; Takashi Emura; David L. Hughes; Shane Krska; Robert A. Reamer; Michael Palucki; Nobuyoshi Yasuda; Paul J. Reider

doi:10.1002/1521-3773(20020603)41:11<1929::AID-ANIE1929>3.0.CO;2-O

Designed ligands as probes for the catalytic binding mode in Mo-catalyzed asymmetric allylic alkylation

Barry M. Trost, Kalindi Dogra, Iwao Hachiya, Takashi Emura, David L. Hughes, Shane Krska, Robert A. Reamer, Michael Palucki, Nobuyoshi Yasuda, Paul J. Reider

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

98 Scopus citations

Abstract

Unusual coordination in the asymmetric allylic alkylation catalyzed by molybdenum (see scheme) was revealed by a study on several ligands, for example, 1. Unexpectedly, only the nitrogen atom of one picolinamide group coordinates to Mo, while the other amide group rigidifies the system. Based on the effectiveness of the bisdeprotonated ligand, the observed reaction can be rationalized and new ligands can be designed for asymmetric induction in allylic alkylations.

Original language	English (US)
Pages (from-to)	1929-1932
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	11
DOIs	https://doi.org/10.1002/1521-3773(20020603)41:11<1929::AID-ANIE1929>3.0.CO;2-O
State	Published - Jun 3 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)

Keywords

Allylic compounds
Asymmetric catalysis
Ligand design
Molybdenum
Regioselectivity

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10.1002/1521-3773(20020603)41:11<1929::AID-ANIE1929>3.0.CO;2-O

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Trost, B. M., Dogra, K., Hachiya, I., Emura, T., Hughes, D. L., Krska, S., Reamer, R. A., Palucki, M., Yasuda, N., & Reider, P. J. (2002). Designed ligands as probes for the catalytic binding mode in Mo-catalyzed asymmetric allylic alkylation. Angewandte Chemie - International Edition, 41(11), 1929-1932. https://doi.org/10.1002/1521-3773(20020603)41:11<1929::AID-ANIE1929>3.0.CO;2-O

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abstract = "Unusual coordination in the asymmetric allylic alkylation catalyzed by molybdenum (see scheme) was revealed by a study on several ligands, for example, 1. Unexpectedly, only the nitrogen atom of one picolinamide group coordinates to Mo, while the other amide group rigidifies the system. Based on the effectiveness of the bisdeprotonated ligand, the observed reaction can be rationalized and new ligands can be designed for asymmetric induction in allylic alkylations.",

keywords = "Allylic compounds, Asymmetric catalysis, Ligand design, Molybdenum, Regioselectivity",

author = "Trost, {Barry M.} and Kalindi Dogra and Iwao Hachiya and Takashi Emura and Hughes, {David L.} and Shane Krska and Reamer, {Robert A.} and Michael Palucki and Nobuyoshi Yasuda and Reider, {Paul J.}",

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doi = "10.1002/1521-3773(20020603)41:11<1929::AID-ANIE1929>3.0.CO;2-O",

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Trost, BM, Dogra, K, Hachiya, I, Emura, T, Hughes, DL, Krska, S, Reamer, RA, Palucki, M, Yasuda, N & Reider, PJ 2002, 'Designed ligands as probes for the catalytic binding mode in Mo-catalyzed asymmetric allylic alkylation', Angewandte Chemie - International Edition, vol. 41, no. 11, pp. 1929-1932. https://doi.org/10.1002/1521-3773(20020603)41:11<1929::AID-ANIE1929>3.0.CO;2-O

TY - JOUR

T1 - Designed ligands as probes for the catalytic binding mode in Mo-catalyzed asymmetric allylic alkylation

AU - Trost, Barry M.

AU - Dogra, Kalindi

AU - Hachiya, Iwao

AU - Emura, Takashi

AU - Hughes, David L.

AU - Krska, Shane

AU - Reamer, Robert A.

AU - Palucki, Michael

AU - Yasuda, Nobuyoshi

AU - Reider, Paul J.

PY - 2002/6/3

Y1 - 2002/6/3

N2 - Unusual coordination in the asymmetric allylic alkylation catalyzed by molybdenum (see scheme) was revealed by a study on several ligands, for example, 1. Unexpectedly, only the nitrogen atom of one picolinamide group coordinates to Mo, while the other amide group rigidifies the system. Based on the effectiveness of the bisdeprotonated ligand, the observed reaction can be rationalized and new ligands can be designed for asymmetric induction in allylic alkylations.

AB - Unusual coordination in the asymmetric allylic alkylation catalyzed by molybdenum (see scheme) was revealed by a study on several ligands, for example, 1. Unexpectedly, only the nitrogen atom of one picolinamide group coordinates to Mo, while the other amide group rigidifies the system. Based on the effectiveness of the bisdeprotonated ligand, the observed reaction can be rationalized and new ligands can be designed for asymmetric induction in allylic alkylations.

KW - Allylic compounds

KW - Asymmetric catalysis

KW - Ligand design

KW - Molybdenum

KW - Regioselectivity

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DO - 10.1002/1521-3773(20020603)41:11<1929::AID-ANIE1929>3.0.CO;2-O

M3 - Article

C2 - 19750636

AN - SCOPUS:0037014083

SN - 1433-7851

VL - 41

SP - 1929

EP - 1932

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 11

ER -

Designed ligands as probes for the catalytic binding mode in Mo-catalyzed asymmetric allylic alkylation

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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