Details

Autor(en) / Beteiligte

• Burghart-Stoll, Heike
• Böhnke, Oliver
• Brückner, Reinhard

Titel

Asymmetric Dihydroxylations of 1-Substituted (E)- and (Z)-3-Methylpent-2-en-4-ynes: Full Compliance with the Sharpless Mnemonic Re-established and Embellished

Ist Teil von

• Organic letters, 2011-03, Vol.13 (5), p.1020-1023

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2011

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Asymmetric dihydroxylations (“ADs”) of the pentenynyl chlorides (E)- and (Z)-1 or the pentenyne-based ester (Z)-3 in the presence of (DHQ)2-containing ligands delivered diol stereoisomers (2R,3S)-2, (2R,3R)-2, and (3S,4R)-4, respectively. The ADs of pentenynyl ethers (E)-10 and (Z)-12, respectively, have the same stereochemical preference under analogous conditions; these reattributions correct previous reports of the contrary. The Sharpless mnemonic rationalizes all these results implying that each substrate prefers a Sharpless/Norrby instead of a Chapleur orientation in the transition state.