Efficient synthesis of chiral acetylene dithioethers in enantiomerically pure form

✍ Scribed by Jaume Balsells; Albert Moyano; Miquel A. Pericàs; Antoni Riera

• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 332 KB
• Volume: 8
• Category: Article
• ISSN: 0957-4166
• DOI: 10.1016/s0957-4166(97)00126-2

✦ Synopsis

Chiral acetylene dithioethers have been synthesized by the first time in enantiomerically pure form through a high yield (93-100%), one-pot procedure involving the successive treatment of trichloroethylene with three equivalents of lithium bis(trimethylsilyl)amide and two equivalents of a chiral thiol in diethyl ether solution. (~) 1997 Elsevier Science Ltd Acetylenic dithioethers 1 are electron rich alkynes which present a high interest as synthetic intermediates. 1 Also due to the electronic nature of their triple bonds, they are promising ligands and reagents for co-ordination chemistry.2 Some years ago, we reported a broad scope, highly efficient synthesis of these species (Scheme 1) taking place as a one-pot procedure from trichloroethylene. 3 CI CI 1) 3.2 eq. KH; THF .

C 2) 2.0 eq. RSH