Development of α-Borylmethyl-(Z)-crotylboronate Reagent and Enantioselective Syntheses of (E)-δ-Hydroxymethyl-syn-homoallylic Alcohols via Highly Stereoselective Allylboration,Organic Letters

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Development of α-Borylmethyl-(Z)-crotylboronate Reagent and Enantioselective Syntheses of (E)-δ-Hydroxymethyl-syn-homoallylic Alcohols via Highly Stereoselective Allylboration
Organic Letters ( IF 4.9 ) Pub Date : 2021-12-03 , DOI: 10.1021/acs.orglett.1c03628
Jiaming Liu ₁ , Shang Gao ₁ , Ming Chen ₁

Affiliation

We report herein the development of α-borylmethyl-(Z)-crotylboronate reagent and the application in highly stereo- and enantioselective syntheses of (E)-δ-hydroxymethyl-syn-homoallylic alcohols. Starting from 1,4-pentadiene, α-borylmethyl-(Z)-crotylboronate was synthesized in two steps with high Z-selectivity and enantioselectivity. Subsequent aldehyde allylboration with the developed boron reagent gave highly enantioenriched (E)-δ-hydroxymethyl-syn-homoallylic alcohols upon oxidative workup.

中文翻译：

α-硼基甲基-(Z)-巴豆基硼酸酯试剂的开发和通过高度立体选择性烯丙基硼化合成(E)-δ-羟甲基-顺-高烯丙基醇的对映选择性

我们在此报告了α-硼基甲基-( Z )-巴豆基硼酸酯试剂的开发以及在( E )-δ-羟甲基顺-高烯丙醇的高度立体选择性和对映选择性合成中的应用。以1,4-戊二烯为原料，分两步合成了α-硼基甲基-( Z )-巴豆基硼酸酯，具有较高的Z-选择性和对映选择性。随后用开发的硼试剂进行醛烯丙基硼化，在氧化处理后得到高度对映体富集的 ( E )-δ-羟甲基-顺-高烯丙基醇。

更新日期：2021-12-17

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