Sulfoximine version of double elimination protocol for synthesis of chiral acetylenic cyclophanes
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Akihiro Orita1, De Lie An, Takehiko Nakano
1Department of Applied Chemistry Okayama University of Science, Japan.
Abstract:
A new strategy for constructing enantiopure acetylenic cyclophanes is described on the basis of one-pot double elimination reaction starting from dialdehydes and bis(sulfoximine)s. In this case, the conventional sulfone protocol affords poorer yields of the desired cyclophanes. Thus, arylene-ethynylene moieties with terminal sulfoximine or formyl functions are linked to binaphthyl cores and these building blocks are then subjected to double elimination reaction. The desired macrocycles are obtained in up to 35 % yield. The corresponding Sonogashira coupling fails to afford cyclophanes indicative of effectiveness of the double elimination methodology.
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