dienyl pinacol boronic ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: dienyl pinacol boronic ester
• 英文别名: 2-Buta-1,3-dienyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 化学式: C₁₀H₁₇BO₂
• 分子量: 180.055
• InChiKey: HUUYPRUYJXORBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dienyl pinacol boronic ester 在 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 copper(l) chloride 、 sodium hydroxide 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.17h， 生成 rac-triethyl(((1S,2S,E)-4-iodo-1-phenyl-2-((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl)but-3-en-1-yl)oxy)silane
  参考文献：
  名称：

  二烯基硼酸酯的催化碳硼化以立体选择性地合成（E）-γ'，δ-双硼基-抗同型烯丙基醇†

  摘要：

  开发了一种铜催化的（E）-γ'，δ-双硼烷基-抗同型烯丙基醇的立体选择性合成。产物含有烷基和乙烯基硼酸酯基团，其可直接用于各种后续转化中。

  DOI：

  10.1039/c9cc04787e

文献信息

• Enantioselective <i>anti</i>- and <i>syn</i>-(Borylmethyl)allylation of Aldehydes via Brønsted Acid Catalysis
  作者：Jiaming Liu、Ming Chen

  DOI：10.1021/acs.orglett.0c03366

  日期：2020.11.20

  The enantioselective anti- and syn-(borylmethyl)allylation of aldehydes via phosphoric acid catalysis is reported. Both (E)- and (Z)-γ-borylmethyl allylboronate reagents were prepared via the Cu-catalyzed highly stereoselective protoboration of 1,3-dienylboronate. Chiral phosphoric acid-catalyzed aldehyde allylation with either the (E)- or (Z)-allylboron reagent provided 1,2-anti- or 1,2-syn-adducts

  对映体选择性的抗-和顺- （borylmethyl）报道通过磷酸催化的醛的烯丙基化。（E）-和（Z）-γ-硼烷基甲基烯丙基硼酸酯试剂都是通过Cu催化的1,3-二烯基硼酸酯的高立体选择性原硼酸酯制备的。用（E）-或（Z）-烯丙基硼试剂进行手性磷酸催化的醛烯丙基化，可提供高收率和高对映选择性的1,2-抗-或1,2-顺式加合物。完成了对morinol D的合成。
• Divergent Access to Benzocycles through Copper‐Catalyzed Borylative Cyclizations
  作者：Wan Seok Yoon、Jung Tae Han、Jaesook Yun

  DOI：10.1002/adsc.202100812

  日期：2021.11.9

  A copper-catalyzed chemodivergent approach to five- and six-membered benzocycles from dienyl arenes tethered with a ketone has been developed. Through proper choice of coordinating ligands and catalytic conditions, copper-catalyzed borylative cyclization of a single dienyl arene can be diverted to two different pathways, leading to indanols and dihydronaphthalenols with high stereoselectivity. The

  已经开发了一种铜催化化学发散方法，用于从与酮相连的二烯基芳烃制备五元和六元苯并环。Through proper choice of coordinating ligands and catalytic conditions, copper-catalyzed borylative cyclization of a single dienyl arene can be diverted to two different pathways, leading to indanols and dihydronaphthalenols with high stereoselectivity. 手性双齿双膦配体 ( S , S )-Ph-BPE 最适用于通过船状过渡态将铜烯丙基不对称加成到系链酮上，而 NHC 配体导致硼烯丙基加成产生具有高非对映选择性的茚满醇。
• Asymmetric Synthesis of 1,2-Dihydronaphthalene-1-ols via Copper-Catalyzed Intramolecular Reductive Cyclization
  作者：Ranjan Kumar Acharyya、Soyoung Kim、Yeji Park、Jung Tae Han、Jaesook Yun

  DOI：10.1021/acs.orglett.0c02829

  日期：2020.10.16

  reductive cyclization of easily accessible benz-tethered 1,3-dienes containing a ketone moiety. This process provided biologically active 1,2-dihydronaphthalene-1-ol derivatives in good yields with excellent enantio- and diastereoselectivity. Mechanistic investigations using density functional theory revealed that (Z)- and (E)-allylcopper intermediates formed in situ from the diene and copper catalyst

  我们描述了铜催化分子内的还原性环化的容易获得的含酮基团的1，3-二烯联苯。该方法以良好的产率提供了具有优异的对映和非对映选择性的生物活性1,2-二氢萘-1-醇衍生物。使用密度泛函理论的机理研究表明，由二烯和铜催化剂原位形成的（Z）-和（E）-烯丙基铜中间体会通过六步反应进行异构化并选择性地对主要产物的（E）-烯丙基铜形式进行分子内烯丙基化。成员船状过渡态。通过烯烃部分的反应将所得产物进一步转化为完全饱和的萘-1-醇。
• Stereoselective Syntheses of (<i>E</i>)-γ′,δ-Bisboryl-Substituted <i>syn</i>-Homoallylic Alcohols via Chemoselective Aldehyde Allylboration
  作者：Mengzhou Wang、Shang Gao、Ming Chen

  DOI：10.1021/acs.orglett.9b00461

  日期：2019.4.5

  the targeted crotylboronate in good yield with high regio- and stereoselectivity. Chemo- and stereoselective addition of this crotylboron reagent to aldehydes followed by protection of the resulting secondary hydroxyl group gave TES-protected homoallylic alcohols bearing an alkyl and a vinyl boronate groups with high stereoselectivities.

  报道了新型（Z）-α，δ-双硼烷基取代的巴豆基硼试剂的开发。镍催化的二烯基硼酸酯的1,4-二硼酸酯化以高收率和高的区域选择性和立体选择性提供了靶向的巴豆基硼酸酯。将该巴豆基硼试剂化学和立体选择性地添加到醛中，然后保护所得的仲羟基，从而得到具有高立体选择性的带有烷基和乙烯基硼酸酯基团的TES保护的均烯丙基醇。
• Enantioselective Syntheses of 1,4-Pentadien-3-yl Carbinols via Brønsted Acid Catalysis
  作者：Shang Gao、Ming Chen

  DOI：10.1021/acs.orglett.9b04089

  日期：2020.1.17

  asymmetric addition of substituted 1,3-pentadienylboronates to aldehydes via Brønsted acid catalysis is reported. Under the developed conditions, a variety of synthetically useful 1,4-pentadien-3-yl carbinols were obtained in good yields with high enantioselectivities in the presence of a catalytic amount of a chiral phosphoric acid.

  据报道，通过布朗斯台德酸催化将不饱和的1,3-戊二烯基硼酸酯不对称加成到醛中。在发达的条件下，在催化量的手性磷酸的存在下，以高收率和高对映选择性获得了各种合成有用的1,4-戊二烯-3-基甲醇。