TY - JOUR
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 - http://www.scopus.com/inward/record.url?scp=33750488744&partnerID=8YFLogxK
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 -