A synthetic and spectroscopic investigation of the asymmetric α-lithiation-trapping of six-membered N-Boc heterocycles using Alexakis diamines

James Firth; Giacomo Gelardi; Peter John Rayner; Darren Stead; Peter Andrew O'Brien

doi:10.3987/COM-18-S(T)87

A synthetic and spectroscopic investigation of the asymmetric α-lithiation-trapping of six-membered N-Boc heterocycles using Alexakis diamines

James Firth, Giacomo Gelardi, Peter John Rayner, Darren Stead, Peter Andrew O'Brien

Chemistry

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

Abstract

The asymmetric lithiation-trapping of six-membered N-Boc heterocycles using s-BuLi and two different Alexakis diamines is reported. These readily available ligands outperform the current ‘best-in-class’ sparteine-type diamines in the lithiation and benzophenone trapping of N-Boc piperazines and the lithiation-cyclisation-trapping of N-Boc-4-chloropiperidine. In situ IR spectroscopy has been used to optimise lithiation times and to discover previously unknown subtleties regarding the lithiation step.

Original language	English
Pages (from-to)	1288-1303
Journal	Heterocycles
Volume	97
Issue number	2
DOIs	https://doi.org/10.3987/COM-18-S(T)87
Publication status	Published - 20 Jun 2018

Bibliographical note

This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.

Access to Document

10.3987/COM-18-S(T)87

Steadotron2-Het-AAM
This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.
Accepted author manuscript, 852 KBLicence: CC BY-NC-ND

Cite this

@article{d8981755ebb74427bd91c60b0e769731,

title = "A synthetic and spectroscopic investigation of the asymmetric α-lithiation-trapping of six-membered N-Boc heterocycles using Alexakis diamines",

abstract = "The asymmetric lithiation-trapping of six-membered N-Boc heterocycles using s-BuLi and two different Alexakis diamines is reported. These readily available ligands outperform the current {\textquoteleft}best-in-class{\textquoteright} sparteine-type diamines in the lithiation and benzophenone trapping of N-Boc piperazines and the lithiation-cyclisation-trapping of N-Boc-4-chloropiperidine. In situ IR spectroscopy has been used to optimise lithiation times and to discover previously unknown subtleties regarding the lithiation step.",

author = "James Firth and Giacomo Gelardi and Rayner, {Peter John} and Darren Stead and O'Brien, {Peter Andrew}",

note = "This is an author-produced version of the published paper. Uploaded in accordance with the publisher{\textquoteright}s self-archiving policy. ",

year = "2018",

month = jun,

day = "20",

doi = "10.3987/COM-18-S(T)87",

language = "English",

volume = "97",

pages = "1288--1303",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "2",

}

TY - JOUR

T1 - A synthetic and spectroscopic investigation of the asymmetric α-lithiation-trapping of six-membered N-Boc heterocycles using Alexakis diamines

AU - Firth, James

AU - Gelardi, Giacomo

AU - Rayner, Peter John

AU - Stead, Darren

AU - O'Brien, Peter Andrew

N1 - This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy.

PY - 2018/6/20

Y1 - 2018/6/20

N2 - The asymmetric lithiation-trapping of six-membered N-Boc heterocycles using s-BuLi and two different Alexakis diamines is reported. These readily available ligands outperform the current ‘best-in-class’ sparteine-type diamines in the lithiation and benzophenone trapping of N-Boc piperazines and the lithiation-cyclisation-trapping of N-Boc-4-chloropiperidine. In situ IR spectroscopy has been used to optimise lithiation times and to discover previously unknown subtleties regarding the lithiation step.

AB - The asymmetric lithiation-trapping of six-membered N-Boc heterocycles using s-BuLi and two different Alexakis diamines is reported. These readily available ligands outperform the current ‘best-in-class’ sparteine-type diamines in the lithiation and benzophenone trapping of N-Boc piperazines and the lithiation-cyclisation-trapping of N-Boc-4-chloropiperidine. In situ IR spectroscopy has been used to optimise lithiation times and to discover previously unknown subtleties regarding the lithiation step.

U2 - 10.3987/COM-18-S(T)87

DO - 10.3987/COM-18-S(T)87

M3 - Article

SN - 0385-5414

VL - 97

SP - 1288

EP - 1303

JO - Heterocycles

JF - Heterocycles

IS - 2

ER -