Stereoselective palladium-catalyzed functionalization of homoallylic alcohols: A convenient synthesis of di- and trisubstituted isoxazolidines and β-amino-δ-hydroxy esters

Malkov A.V.; Bar??g M.; Miller-Potucká L.; Kabeshov M.A.; Farrugia L.J.; Ko?ovsky P.

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Stereoselective palladium-catalyzed functionalization of homoallylic alcohols: A convenient synthesis of di- and trisubstituted isoxazolidines and β-amino-δ-hydroxy esters

机译：立体选择性钯催化均烯丙基醇的官能化：二取代和三取代的异恶唑烷和β-氨基-δ-羟基酯的便捷合成

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Enantiopure, Boc-protected alkoxyamines 12 and 13, derived from the readily available homoallylic alcohols 4 via a reaction that involves either inversion or retention of configuration, undergo a diastereoselective Pd-catalyzed ring-closing carbonylative amidation to produce isoxazolidines 16/17 (≤50:1 diastereoisomer ratio (d.r.)) that can be readily converted into the N-Boc-protected esters of β-hydroxy acids and their substituted homologues 37. The key carbonylative cyclization proceeds through an unusual syn addition of the palladium and the nitrogen nucleophile across the CiC bond (19→21), as revealed by the reaction of 15, which afforded isoxazolidine 18 with high diastereoselectivity.

机译：对映纯的，由Boc保护的烷氧基胺12和13通过容易涉及的转化或保留构型的反应衍生自易得的均丙醇4，进行非对映选择性Pd催化的闭环羰基酰胺化反应生成异恶唑烷16/17（≤50 1：1的非对映异构体比率（dr），可以很容易地转化为N-Boc保护的β-羟基酸的酯及其取代的同系物37.关键的羰基化环化反应是通过钯和氮亲核试剂的不寻常的同加15的反应揭示了CiC键（19→21），得到具有高非对映选择性的异恶唑烷18。

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《Chemistry: A European journal》 |2012年第22期|共12页
作者
Malkov A.V.; Bar??g M.; Miller-Potucká L.; Kabeshov M.A.; Farrugia L.J.; Ko?ovsky P.;
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正文语种 eng
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amidopalladation; amino acids; carbonylation; palladium; stereocontrol;

机译：酰胺基钯;氨基酸;羰基化;钯;立体控制;

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1. Stereoselective palladium-catalyzed functionalization of homoallylic alcohols: A convenient synthesis of di- and trisubstituted isoxazolidines and β-amino-δ-hydroxy esters [J] . Malkov A.V., Bar??g M., Miller-Potucká L., Chemistry: A European journal . 2012,第22期

机译：立体选择性钯催化均烯丙基醇的官能化：二取代和三取代的异恶唑烷和β-氨基-δ-羟基酯的便捷合成
2. Synthesis of Alkenylboronic Esters: An Alternative Route to Trisubstituted Homoallylic Alcohols [J] . Gehrke Yvonne, Berg Christina Annette, Vahabi Roza, European journal of organic chemistry . 2016,第14期

机译：烯基硼酸酯的合成：三取代均烯丙基醇的替代途径
3. Highly Stereoselective Synthesis of Functionalized β,β-Di- and Trisubstituted Vinylic Sulfoxides by Cu-Catalyzed Conjugate Addition of Organozinc Reagents [J] . Naoyoshi Maezaki, Hiroaki Sawamoto, Tomoko Suzuki, The Journal of Organic Chemistry . 2004,第24期

机译：铜催化共轭添加有机锌试剂可高度立体选择性合成功能化的β，β-二-和三取代乙烯基亚砜。
4. Stereoselective Synthesis of δ-Silyl-Substituted anti-Homoallylic Alcohols Using Palladium-Catalyzed Three-Component Reaction [C] . MURAKAMI Miki, HORINO Yoshikazu, ABE Hitoshi 日本化学会春季年会講演予稿集 . 2018

机译：使用钯催化的三组分反应的δ-甲硅烷基取代的抗官能醇的立体选择性合成
5. Exploration of alpha-Diazocarbonyl Compounds for Transition-Metal Catalyzed Carbon-Carbon Bond Formations. Development of Palladium-Catalyzed Stereoselective Synthesis of Trisubstituted Alkenes and the Synthesis of Quaternary alpha,alpha-Heterodiaryl Carboxylic Acids by Rhodium-Catalyzed Multi-Component Coupling Reactions. [D] . Tsoi, Yuk Tai. 2012

机译：探索用于过渡金属催化的碳-碳键形成的α-重氮羰基化合物。铑催化的多组分偶合反应在钯催化的立体选择性合成三取代的烯烃上的发展和季铵的α，α-杂二芳基羧酸的合成。
6. Asymmetric Synthesis of anti-β-Amino-α-Hydroxy Esters via Dynamic Kinetic Resolution of β-Amino-α-Keto Esters [O] . C. Guy Goodman, Dung T. Do, Jeffrey S. Johnson -1

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7. Gallium-Mediated Allyl Transfer from Bulky Homoallylic Alcohol to Aldehydes via Retro-allylation: Stereoselective Synthesis of Both erythro- and threo-Homoallylic Alcohols11 [O] . -1

机译：镓介导的烯丙基通过复古 - 烯丙基化从庞大的统一醇转移到醛：异形选择性合成红细胞和Threo-Homoallic醇的11

Stereoselective palladium-catalyzed functionalization of homoallylic alcohols: A convenient synthesis of di- and trisubstituted isoxazolidines and β-amino-δ-hydroxy esters

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