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通过炔烃卤硼化、锆催化的烯烃不对称碳铝化反应（ZACA反应）以及钯催化的串联根岸偶联反应高效立体选择性合成黄粉虫性信息素。

Efficient and stereoselective synthesis of yellow scale pheromone via alkyne haloboration, Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction), and Pd-catalyzed tandem Negishi coupling.

作者信息

Xu Zhaoqing, Negishi Ei-Ichi

机构信息

Herbert C. Brown Laboratories of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.

出版信息

Org Lett. 2008 Oct 2;10(19):4311-4. doi: 10.1021/ol8017566. Epub 2008 Sep 3.

DOI:10.1021/ol8017566
PMID:18763786
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2774748/
Abstract

A Pd-catalyzed reaction of allylzincs with the 1-octyne bromoboration product gives the desired allyl-alkenyl coupling products in good yields except with H 2CCHCH 2ZnBr. This reaction is suitable for converting an alkyne bromoboration product 3 into 4 with no isomerization or beta-elimination. The Pd-catalyzed isoalkyl-alkenyl coupling of 4 with the isoalkylzinc reagent derived from 2 provides yellow scale pheromone ( 1) of >/=98% isomeric purity in 34% in six steps from TBDPS-protected homoallyl alcohol.

摘要

钯催化烯丙基锌与1-辛炔硼溴化产物的反应，除了与H₂CCHCH₂ZnBr反应外，能以良好的产率得到所需的烯丙基-烯基偶联产物。该反应适用于将炔烃硼溴化产物3转化为4，且无异构化或β-消除反应。钯催化4与由2衍生的异烷基锌试剂进行异烷基-烯基偶联反应，从叔丁基二苯基硅烷基保护的高烯丙醇出发，经过六步反应，以34%的产率得到异构体纯度≥98%的黄色鳞翅目昆虫信息素（1）。

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A new protocol for the enantioselective synthesis of methyl-substituted alkanols and their derivatives through a hydroalumination/ zirconium-catalyzed alkylalumination tandem process.一种通过氢化铝化/锆催化的烷基铝化串联过程对甲基取代链烷醇及其衍生物进行对映选择性合成的新方案。
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Recent advances in efficient and selective synthesis of di-, tri-, and tetrasubstituted alkenes via Pd-catalyzed alkenylation-carbonyl olefination synergy.通过钯催化的烯基化-羰基烯化协同作用高效选择性合成二取代、三取代和四取代烯烃的最新进展。
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Efficient and selective synthesis of (S,R,R,S,R,S)-4,6,8,10,16,18-hexamethyl-docosane via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction).通过锆催化的烯烃不对称碳铝化反应（ZACA反应）高效且选择性地合成（S，R，R，S，R，S）-4,6,8,10,16,18-六甲基二十二烷。
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Fully reagent-controlled asymmetric synthesis of (-)-spongidepsin via the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction).通过锆催化的烯烃不对称碳铝化反应（ZACA反应）实现（-）-海绵抑肽素的全试剂控制不对称合成。
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