Diastereo- and Enantioselective Synthesis of (E)-2-Methyl-1,2-syn- and (E)-2-Methyl-1,2-anti-3-pentenediols via Allenylboronate Kinetic Resolution with (dIpc)2BH and Aldehyde Allylboration

Jeng-Liang Han (2073691)
Ming Chen (115604)
William R. Roush (361839)

Publication date

June 2012

DOI

Abstract

Enantioselective hydroboration of racemic allenylboronate (±)-1 with 0.48 equiv of (dIpc)2BH at −25 °C proceeds with efficient kinetic resolution and provides allylborane (R)-Z-4. When heated to 95 °C, allylborane (R)-Z-4 isomerizes to the thermodynamically more stable allylborane isomer (S)-E-7. Subsequent allylboration of aldehydes with (R)-Z-4 or (S)-E-7 at −78 °C followed by oxidative workup provides 1,2-syn- or 1,2-anti-diols, 2 or 3, respectively, in 87–94% ee

Extracted data

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Diastereo- and Enantioselective Synthesis of (<i>E</i>)-2-Methyl-1,2-<i>syn</i>- and (<i>E</i>)-2-Methyl-1,2-<i>anti</i>-3-pentenediols via Allenylboronate Kinetic Resolution with (<sup><i>d</i></sup>Ipc)<sub>2</sub>BH and Aldehyde Allylboration

Abstract

Extracted data

Diastereo- and Enantioselective Synthesis of (<i>E</i>)-2-Methyl-1,2-<i>syn</i>- and (<i>E</i>)-2-Methyl-1,2-<i>anti</i>-3-pentenediols via Allenylboronate Kinetic Resolution with (<sup><i>d</i></sup>Ipc)<sub>2</sub>BH and Aldehyde Allylboration

Abstract

Extracted data

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