Simultaneous and stereoselective formation of planar and axial chiralities in enantiopure sulfinyl iron diene complexes

Robert S. Paley; Jane M. Liu; Bruce R. Lichtenstein; Vanessa L. Knoedler; Toby T. Sanan; Drew J. Adams; Jorge Fernández; Paul R. Rablen

doi:10.1021/ol027306q

Simultaneous and stereoselective formation of planar and axial chiralities in enantiopure sulfinyl iron diene complexes

Robert S. Paley^*, Jane M. Liu, Bruce R. Lichtenstein, Vanessa L. Knoedler, Toby T. Sanan, Drew J. Adams, Jorge Fernández, Paul R. Rablen

^*Corresponding author for this work

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

Abstract

Enantiopure (1Z,3E)-1-sulfinyl dienes bearing an o-dithianylphenyl group can be prepared and complexed with (bda)Fe(CO) ₃ to afford the corresponding sulfinyl diene iron(0) tricarbonyl complexes. This diastereoselective complexation introduces planar and axial chirality simultaneously, with a high degree of facial selectivity as well as atropselectivity. Dynamic kinetic resolution is likely to be the origin of the atropselectivity.

Original language	English
Pages (from-to)	309-312
Number of pages	4
Journal	Organic Letters
Volume	5
Issue number	3
Early online date	9 Jan 2003
DOIs	https://doi.org/10.1021/ol027306q
Publication status	Published - 1 Feb 2003

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@article{12864a2d54a84a6aa0d3727769d4048b,

title = "Simultaneous and stereoselective formation of planar and axial chiralities in enantiopure sulfinyl iron diene complexes",

abstract = "Enantiopure (1Z,3E)-1-sulfinyl dienes bearing an o-dithianylphenyl group can be prepared and complexed with (bda)Fe(CO) 3 to afford the corresponding sulfinyl diene iron(0) tricarbonyl complexes. This diastereoselective complexation introduces planar and axial chirality simultaneously, with a high degree of facial selectivity as well as atropselectivity. Dynamic kinetic resolution is likely to be the origin of the atropselectivity.",

author = "Paley, \{Robert S.\} and Liu, \{Jane M.\} and Lichtenstein, \{Bruce R.\} and Knoedler, \{Vanessa L.\} and Sanan, \{Toby T.\} and Adams, \{Drew J.\} and Jorge Fern{\'a}ndez and Rablen, \{Paul R.\}",

year = "2003",

month = feb,

day = "1",

doi = "10.1021/ol027306q",

language = "English",

volume = "5",

pages = "309--312",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Simultaneous and stereoselective formation of planar and axial chiralities in enantiopure sulfinyl iron diene complexes

AU - Paley, Robert S.

AU - Liu, Jane M.

AU - Lichtenstein, Bruce R.

AU - Knoedler, Vanessa L.

AU - Sanan, Toby T.

AU - Adams, Drew J.

AU - Fernández, Jorge

AU - Rablen, Paul R.

PY - 2003/2/1

Y1 - 2003/2/1

N2 - Enantiopure (1Z,3E)-1-sulfinyl dienes bearing an o-dithianylphenyl group can be prepared and complexed with (bda)Fe(CO) 3 to afford the corresponding sulfinyl diene iron(0) tricarbonyl complexes. This diastereoselective complexation introduces planar and axial chirality simultaneously, with a high degree of facial selectivity as well as atropselectivity. Dynamic kinetic resolution is likely to be the origin of the atropselectivity.

AB - Enantiopure (1Z,3E)-1-sulfinyl dienes bearing an o-dithianylphenyl group can be prepared and complexed with (bda)Fe(CO) 3 to afford the corresponding sulfinyl diene iron(0) tricarbonyl complexes. This diastereoselective complexation introduces planar and axial chirality simultaneously, with a high degree of facial selectivity as well as atropselectivity. Dynamic kinetic resolution is likely to be the origin of the atropselectivity.

UR - https://www.scopus.com/pages/publications/0141518288

U2 - 10.1021/ol027306q

DO - 10.1021/ol027306q

M3 - Article

C2 - 12556179

AN - SCOPUS:0141518288

SN - 1523-7060

VL - 5

SP - 309

EP - 312

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Simultaneous and stereoselective formation of planar and axial chiralities in enantiopure sulfinyl iron diene complexes

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