Remarkable effects of a pentafluorophenyl group on the stereoselective reactions of a chiral iron acyl complex

Iwao Ojima; Hyok Boong Kwon

doi:10.1021/ja00225a004

Remarkable effects of a pentafluorophenyl group on the stereoselective reactions of a chiral iron acyl complex

Iwao Ojima
, Hyok Boong Kwon

Chemistry

Stony Brook University

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

51 Scopus citations

Abstract

A novel chiral iron acyl complex, [(C₆F₅)Ph₂P](CO)CpFeCOMe (PFCHIRAC), is synthesized. The stereoselective aidol and imine condensation reactions with benzaldehyde and benzylideneaniline using the lithium, tin, aluminum, and copper enolates of PFCHIRAC are studied. The reactions give (R*,S*) products regardless of the metal enolate species with high stereoselectivities (89-99% de). The observed unique stereodifferentiation is rationalized on the basis of an electron donoracceptor type attractive interaction between the pentafluorophenyl moiety and the enolate oxygen. The variable-temperature NMR (¹H, ¹⁹F, ³¹P) study of the dynamic behavior of PFCHIRAC strongly supports the rationale.

Original language	English
Pages (from-to)	5617-5621
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	110
Issue number	17
DOIs	https://doi.org/10.1021/ja00225a004
State	Published - Aug 1988

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@article{ffa343a806004a20825bd62a746f551a,

title = "Remarkable effects of a pentafluorophenyl group on the stereoselective reactions of a chiral iron acyl complex",

abstract = "A novel chiral iron acyl complex, [(C6F5)Ph2P](CO)CpFeCOMe (PFCHIRAC), is synthesized. The stereoselective aidol and imine condensation reactions with benzaldehyde and benzylideneaniline using the lithium, tin, aluminum, and copper enolates of PFCHIRAC are studied. The reactions give (R*,S*) products regardless of the metal enolate species with high stereoselectivities (89-99\% de). The observed unique stereodifferentiation is rationalized on the basis of an electron donoracceptor type attractive interaction between the pentafluorophenyl moiety and the enolate oxygen. The variable-temperature NMR (1H, 19F, 31P) study of the dynamic behavior of PFCHIRAC strongly supports the rationale.",

author = "Iwao Ojima and Kwon, \{Hyok Boong\}",

year = "1988",

month = aug,

doi = "10.1021/ja00225a004",

language = "English",

volume = "110",

pages = "5617--5621",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

number = "17",

}

TY - JOUR

T1 - Remarkable effects of a pentafluorophenyl group on the stereoselective reactions of a chiral iron acyl complex

AU - Ojima, Iwao

AU - Kwon, Hyok Boong

PY - 1988/8

Y1 - 1988/8

N2 - A novel chiral iron acyl complex, [(C6F5)Ph2P](CO)CpFeCOMe (PFCHIRAC), is synthesized. The stereoselective aidol and imine condensation reactions with benzaldehyde and benzylideneaniline using the lithium, tin, aluminum, and copper enolates of PFCHIRAC are studied. The reactions give (R*,S*) products regardless of the metal enolate species with high stereoselectivities (89-99% de). The observed unique stereodifferentiation is rationalized on the basis of an electron donoracceptor type attractive interaction between the pentafluorophenyl moiety and the enolate oxygen. The variable-temperature NMR (1H, 19F, 31P) study of the dynamic behavior of PFCHIRAC strongly supports the rationale.

AB - A novel chiral iron acyl complex, [(C6F5)Ph2P](CO)CpFeCOMe (PFCHIRAC), is synthesized. The stereoselective aidol and imine condensation reactions with benzaldehyde and benzylideneaniline using the lithium, tin, aluminum, and copper enolates of PFCHIRAC are studied. The reactions give (R*,S*) products regardless of the metal enolate species with high stereoselectivities (89-99% de). The observed unique stereodifferentiation is rationalized on the basis of an electron donoracceptor type attractive interaction between the pentafluorophenyl moiety and the enolate oxygen. The variable-temperature NMR (1H, 19F, 31P) study of the dynamic behavior of PFCHIRAC strongly supports the rationale.

UR - https://www.scopus.com/pages/publications/0000914747

U2 - 10.1021/ja00225a004

DO - 10.1021/ja00225a004

M3 - Article

AN - SCOPUS:0000914747

SN - 0002-7863

VL - 110

SP - 5617

EP - 5621

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 17

ER -

Remarkable effects of a pentafluorophenyl group on the stereoselective reactions of a chiral iron acyl complex

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