Manipulating the diastereoselectivity of ortholithiation in planar chiral ferrocenes

Simon A. Herbert; Dominic C. Castell; Jonathan Clayden; Gareth E. Arnott

doi:10.1021/ol4013734

Manipulating the diastereoselectivity of ortholithiation in planar chiral ferrocenes

Simon A. Herbert
, Dominic C. Castell
, Jonathan Clayden
, Gareth E. Arnott^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

33 Citations (Scopus)

Abstract

The sense of asymmetric ortholithiation directed by a chiral oxazoline may be inverted simply by the choice of achiral ligand. Comparison of results with a number of ferrocenyl oxazoline derivatives suggests that lithiation takes place by coordination to the oxazoline nitrogen irrespective of the ligand used.

Original language	English
Pages (from-to)	3334-3337
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	13
Early online date	25 Jun 2013
DOIs	https://doi.org/10.1021/ol4013734
Publication status	Published - 5 Jul 2013

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Organic & Biological

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title = "Manipulating the diastereoselectivity of ortholithiation in planar chiral ferrocenes",

abstract = "The sense of asymmetric ortholithiation directed by a chiral oxazoline may be inverted simply by the choice of achiral ligand. Comparison of results with a number of ferrocenyl oxazoline derivatives suggests that lithiation takes place by coordination to the oxazoline nitrogen irrespective of the ligand used.",

author = "Herbert, \{Simon A.\} and Castell, \{Dominic C.\} and Jonathan Clayden and Arnott, \{Gareth E.\}",

year = "2013",

month = jul,

day = "5",

doi = "10.1021/ol4013734",

language = "English",

volume = "15",

pages = "3334--3337",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "13",

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TY - JOUR

T1 - Manipulating the diastereoselectivity of ortholithiation in planar chiral ferrocenes

AU - Herbert, Simon A.

AU - Castell, Dominic C.

AU - Clayden, Jonathan

AU - Arnott, Gareth E.

PY - 2013/7/5

Y1 - 2013/7/5

N2 - The sense of asymmetric ortholithiation directed by a chiral oxazoline may be inverted simply by the choice of achiral ligand. Comparison of results with a number of ferrocenyl oxazoline derivatives suggests that lithiation takes place by coordination to the oxazoline nitrogen irrespective of the ligand used.

AB - The sense of asymmetric ortholithiation directed by a chiral oxazoline may be inverted simply by the choice of achiral ligand. Comparison of results with a number of ferrocenyl oxazoline derivatives suggests that lithiation takes place by coordination to the oxazoline nitrogen irrespective of the ligand used.

UR - https://www.scopus.com/pages/publications/84880011109

U2 - 10.1021/ol4013734

DO - 10.1021/ol4013734

M3 - Article (Academic Journal)

C2 - 23826677

AN - SCOPUS:84880011109

SN - 1523-7060

VL - 15

SP - 3334

EP - 3337

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Manipulating the diastereoselectivity of ortholithiation in planar chiral ferrocenes

Abstract

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