A practical synthesis of a [2.2.1] bicyclic chiral sulfide for asymmetric transformations

Varinder K. Aggarwal; Guangyu Fang; Christoforos G. Kokotos; Jeffery Richardson; Matthew G. Unthank

doi:10.1016/j.tet.2006.06.044

A practical synthesis of a [2.2.1] bicyclic chiral sulfide for asymmetric transformations

Varinder K. Aggarwal^*, Guangyu Fang, Christoforos G. Kokotos, Jeffery Richardson, Matthew G. Unthank

^*Corresponding author for this work

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

33 Citations (Scopus)

Abstract

A substantially improved synthesis of synthetically useful chiral sulfide 1 is described. Starting from (+)-10-camphorsulfonic acid, the chiral sulfide was synthesised on large scale in five steps and 56% overall yield. Significant improvements include the use of Bu₃P in place of Ph₃P for the reduction of the chlorosulfonyl group to the thiol, allowing removal of phosphine oxide by aqueous extraction and improvements in the photochemistry using either a modified batch reactor or a single pass continuous flow reactor.

Original language	English
Pages (from-to)	11297-11303
Number of pages	7
Journal	Tetrahedron
Volume	62
Issue number	49
DOIs	https://doi.org/10.1016/j.tet.2006.06.044
Publication status	Published - 4 Dec 2006
Externally published	Yes

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10.1016/j.tet.2006.06.044

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title = "A practical synthesis of a [2.2.1] bicyclic chiral sulfide for asymmetric transformations",

abstract = "A substantially improved synthesis of synthetically useful chiral sulfide 1 is described. Starting from (+)-10-camphorsulfonic acid, the chiral sulfide was synthesised on large scale in five steps and 56\% overall yield. Significant improvements include the use of Bu3P in place of Ph3P for the reduction of the chlorosulfonyl group to the thiol, allowing removal of phosphine oxide by aqueous extraction and improvements in the photochemistry using either a modified batch reactor or a single pass continuous flow reactor.",

author = "Aggarwal, \{Varinder K.\} and Guangyu Fang and Kokotos, \{Christoforos G.\} and Jeffery Richardson and Unthank, \{Matthew G.\}",

note = "Funding Information: We thank EPSRC, GlaxoSmithKline (Nigel Hussain), NPILpharma (Robin Fieldhouse), Johnson Matthey (Mark Hooper), Syngenta (David Ritchie), and the DTI for financial support. We thank Professor Kevin Booker-Milburn for advice and access to his photochemical apparatus. ",

year = "2006",

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doi = "10.1016/j.tet.2006.06.044",

language = "English",

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pages = "11297--11303",

journal = "Tetrahedron",

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T1 - A practical synthesis of a [2.2.1] bicyclic chiral sulfide for asymmetric transformations

AU - Aggarwal, Varinder K.

AU - Fang, Guangyu

AU - Kokotos, Christoforos G.

AU - Richardson, Jeffery

AU - Unthank, Matthew G.

N1 - Funding Information: We thank EPSRC, GlaxoSmithKline (Nigel Hussain), NPILpharma (Robin Fieldhouse), Johnson Matthey (Mark Hooper), Syngenta (David Ritchie), and the DTI for financial support. We thank Professor Kevin Booker-Milburn for advice and access to his photochemical apparatus.

PY - 2006/12/4

Y1 - 2006/12/4

N2 - A substantially improved synthesis of synthetically useful chiral sulfide 1 is described. Starting from (+)-10-camphorsulfonic acid, the chiral sulfide was synthesised on large scale in five steps and 56% overall yield. Significant improvements include the use of Bu3P in place of Ph3P for the reduction of the chlorosulfonyl group to the thiol, allowing removal of phosphine oxide by aqueous extraction and improvements in the photochemistry using either a modified batch reactor or a single pass continuous flow reactor.

AB - A substantially improved synthesis of synthetically useful chiral sulfide 1 is described. Starting from (+)-10-camphorsulfonic acid, the chiral sulfide was synthesised on large scale in five steps and 56% overall yield. Significant improvements include the use of Bu3P in place of Ph3P for the reduction of the chlorosulfonyl group to the thiol, allowing removal of phosphine oxide by aqueous extraction and improvements in the photochemistry using either a modified batch reactor or a single pass continuous flow reactor.

UR - https://www.scopus.com/pages/publications/33750488744

U2 - 10.1016/j.tet.2006.06.044

DO - 10.1016/j.tet.2006.06.044

M3 - Article

AN - SCOPUS:33750488744

SN - 0040-4020

VL - 62

SP - 11297

EP - 11303

JO - Tetrahedron

JF - Tetrahedron

IS - 49

ER -

A practical synthesis of a [2.2.1] bicyclic chiral sulfide for asymmetric transformations

Abstract

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