Enthalpy- and/or entropy-controlled asymmetric oxidation: Stereocontrolling factors in Mn-salen-catalyzed oxidation

T. Nishida; A. Miyafuji; Y. N. Ito; T. Katsuki

doi:10.1016/S0040-4039(00)01210-7

Enthalpy- and/or entropy-controlled asymmetric oxidation: Stereocontrolling factors in Mn-salen-catalyzed oxidation

T. Nishida, A. Miyafuji, Y. N. Ito, T. Katsuki

Organic and Biological Chemistry

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

30 Citations (Scopus)

Abstract

The degree of enantioselection by second-generation Mn-salen complexes was found to depend upon the conformation of their ligand and substrate nucleophilicity. Oxidation of usual olefins was better effected by using (R,S)-Mn-salen complexes as catalysts, while that of more nucleophilic ones was achieved by using (R,R)-Mn-salen complexes. This phenomenon was explained by analyzing the enthalpy and entropy factors of the reactions. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	7053-7058
Number of pages	6
Journal	Tetrahedron Letters
Volume	41
Issue number	36
DOIs	https://doi.org/10.1016/S0040-4039(00)01210-7
Publication status	Published - Sept 2 2000

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/S0040-4039(00)01210-7

Cite this

@article{82739d1ee0a64c138e1350e33a937bed,

title = "Enthalpy- and/or entropy-controlled asymmetric oxidation: Stereocontrolling factors in Mn-salen-catalyzed oxidation",

abstract = "The degree of enantioselection by second-generation Mn-salen complexes was found to depend upon the conformation of their ligand and substrate nucleophilicity. Oxidation of usual olefins was better effected by using (R,S)-Mn-salen complexes as catalysts, while that of more nucleophilic ones was achieved by using (R,R)-Mn-salen complexes. This phenomenon was explained by analyzing the enthalpy and entropy factors of the reactions. (C) 2000 Elsevier Science Ltd.",

author = "T. Nishida and A. Miyafuji and Ito, {Y. N.} and T. Katsuki",

note = "Funding Information: Financial support from a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan, is gratefully acknowledged.",

year = "2000",

month = sep,

day = "2",

doi = "10.1016/S0040-4039(00)01210-7",

language = "English",

volume = "41",

pages = "7053--7058",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "36",

}

TY - JOUR

T1 - Enthalpy- and/or entropy-controlled asymmetric oxidation

T2 - Stereocontrolling factors in Mn-salen-catalyzed oxidation

AU - Nishida, T.

AU - Miyafuji, A.

AU - Ito, Y. N.

AU - Katsuki, T.

N1 - Funding Information: Financial support from a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan, is gratefully acknowledged.

PY - 2000/9/2

Y1 - 2000/9/2

N2 - The degree of enantioselection by second-generation Mn-salen complexes was found to depend upon the conformation of their ligand and substrate nucleophilicity. Oxidation of usual olefins was better effected by using (R,S)-Mn-salen complexes as catalysts, while that of more nucleophilic ones was achieved by using (R,R)-Mn-salen complexes. This phenomenon was explained by analyzing the enthalpy and entropy factors of the reactions. (C) 2000 Elsevier Science Ltd.

AB - The degree of enantioselection by second-generation Mn-salen complexes was found to depend upon the conformation of their ligand and substrate nucleophilicity. Oxidation of usual olefins was better effected by using (R,S)-Mn-salen complexes as catalysts, while that of more nucleophilic ones was achieved by using (R,R)-Mn-salen complexes. This phenomenon was explained by analyzing the enthalpy and entropy factors of the reactions. (C) 2000 Elsevier Science Ltd.

UR - http://www.scopus.com/inward/record.url?scp=0034596445&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034596445&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(00)01210-7

DO - 10.1016/S0040-4039(00)01210-7

M3 - Article

AN - SCOPUS:0034596445

SN - 0040-4039

VL - 41

SP - 7053

EP - 7058

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 36

ER -

Enthalpy- and/or entropy-controlled asymmetric oxidation: Stereocontrolling factors in Mn-salen-catalyzed oxidation

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this