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Synthesis of Enantiopure Tertiary Skipped Diynes via One-Pot Desymmetrizing TMS-Cleavage

Abstract : Enantiopure tetrasubstituted skipped diynes were readily synthesized from N-protected amino esters upon addition of lithium TMS-acetylide which was found to be desymmetrizing through one-pot selective TMS-cleavage. The deprotection of the TMS group was realized through a one-pot silicon atom attack by the liberated methoxide, which was diastereoselective due to a conformational favorable chelate.
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https://hal-amu.archives-ouvertes.fr/hal-01460404
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Submitted on : Tuesday, February 7, 2017 - 4:39:15 PM
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Malek Nechab, Nicolas Vanthuyne. Synthesis of Enantiopure Tertiary Skipped Diynes via One-Pot Desymmetrizing TMS-Cleavage. Organic Letters, American Chemical Society, 2012, 14 (15), pp.3974--3977. ⟨10.1021/ol3017462⟩. ⟨hal-01460404⟩

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