Progressive Studies on the Novel Samarium-Catalyzed Diastereoselective Tandem Semipinacol Rearrangement/Tishchenko Reduction of Secondary alpha-Hydroxy Epoxides

Chun-An Fan; Xiang-Dong Hu; Yong-Qiang Tu; Bao-Min Wang; Zhen-Lei Song

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Progressive Studies on the Novel Samarium-Catalyzed Diastereoselective Tandem Semipinacol Rearrangement/Tishchenko Reduction of Secondary alpha-Hydroxy Epoxides

机译：新型Sa催化的非对映选择性串联半频哪醇重排/ Tishchenko还原α-羟基环氧化合物的进展研究

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摘要

A novel and highly diastereoselective samarium-catalyzed tandem rearrangement/reductionof secondary alpha-hydroxy epoxides,which involves a C1 to C3 carbon migration rearrangement and a very interesting hetero-Tishchenko reduction of the intermediate aldehyde and the reductant aldehyde,has been reported.This reaction could be developed to provide a facile and stereoselective construction of 2-quarternary 1,3-diol units with an hydroxymethyl moiety attached to the diastereogenic quaternary carbon center.Detailed investigations have been carried out concerning the screening of the aldehydes as a reductant,the optimization of reaction conditions,and the substrate scope of this tandem reaction.A catalytic cycle for this reaction,the electronic and steric effects of the reductant aldehydes,and the mechanism for the acyl migration of 1,3-diol monoesters are proposed.

机译：据报道，一种新颖且高度非对映选择性的mar催化串联重排/还原仲α-羟基环氧化物，涉及C1至C3的碳迁移重排以及中间醛和还原醛的非常有趣的Tishchenko还原。可以开发出一种简便，立体选择性的结构，使2-季铵基1,3-二醇单元的羟甲基部分与非对映异构的季碳中心相连。对作为还原剂的醛的筛选进行了详细研究，提出了该反应的催化循环，还原醛的电子和空间效应，以及1，3-二醇单酯的酰基迁移机理。

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《Chemistry: A European journal》 |2003年第18期|共10页
作者
Chun-An Fan; Xiang-Dong Hu; Yong-Qiang Tu; Bao-Min Wang; Zhen-Lei Song;
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正文语种 eng
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alcohols; diastereoselectivity; rearrangement; samarium; tishchenko reaction;

机译：醇;非对映选择性;重排;sa;季申科反应;

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1. Progressive Studies on the Novel Samarium-Catalyzed Diastereoselective Tandem Semipinacol Rearrangement/Tishchenko Reduction of Secondary alpha-Hydroxy Epoxides [J] . Chun-An Fan, Xiang-Dong Hu, Yong-Qiang Tu, Chemistry: A European journal . 2003,第18期

机译：新型Sa催化的非对映选择性串联半频哪醇重排/ Tishchenko还原α-羟基环氧化合物的进展研究
2. Kinetic resolution via semipinacol rearrangement of alpha-hydroxy epoxides: a new method for asymmetric synthesis of alpha-hydroxy epoxides and beta-hydroxy ketones containing an alpha-quaternary carbon [J] . Wang F., Tu YQ., Fan CA., Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2002,第4期

机译：通过半频哪醇重排α-羟基环氧化物的动力学拆分：一种不对称合成α-羟基环氧化物和含α-季碳的β-羟基酮的新方法
3. Extensive Studies on the AIEt3/THF-Promoted Diastereoselective Tandem Rearrangement/Reduction of α-Hydroxy (Amino) Heterocyclopropane:An Efficient Approach to 2-Quaternary 1,3-Diheteroatom Units [J] . LIXin(李心), WANGBao-Min(王保民), ZHAOXue-Zhi(赵学智), 中国化学（英文版） . 2004,第010期

机译：AIEt3 / THF促进的非对映选择性串联重排/还原的α-羟基（氨基）杂环丙烷的广泛研究：一种有效的方法来2季1，3-二杂原子单元
4. Highly Diastereoselective Tandem Reduction-Allylation Reactions of 1,4-Diketones with Zirconocene-Olefin Complexes [C] . Kazuya Fujita, Hiroshi Shinokubo, Koichiro Oshima Symposium on Organometallic Chemistry . 2003

机译：用锆茂 - 烯烃配合物的1,4-二酮的高度映射串联酸化 - 烯丙基化反应
5. Part A. Diastereoselective synthesis of protected secondary amines via reduction /alkylation or deprotonation /alkylation of N-diphenylphosphinylimines. Part B. Synthesis of secondary amines via 1,2-addition of organometallic reagents to N-diphenylphosphinylimines and subsequent alkylation [D] . Shin, Hyunshun 2001

机译：A部分：通过N-二苯基膦亚胺的还原/烷基化或去质子化/烷基化的非对映选择性合成保护的仲胺。 B部分：通过将有机金属试剂1,2-加成到N-二苯基膦亚胺和随后的烷基化反应来合成仲胺
6. Facile access to diverse all-carbon quaternary center containing spirobicycles by exploring a tandem Castro–Stephens coupling/acyloxy shift/cyclization/semipinacol rearrangement sequence [O] . Ye Zhang, Tian-Lu Zheng, Fu Cheng, 2020

机译：通过探索串联Castro-Stephens偶联/酰氧基移/环化/半藻醇重排序列可以进入含有螺旋自动剪辑的各种全碳四元度中心
7. Diastereoselective Synthesis of Tetrahydrofurans via Mead Reductive Cyclization of Keto-b-Lactones Derived from the Tandem Mukaiyama Aldol Lactonization (TMAL) Process [O] . -1

机译：通过串联Mukaiyama aldol缺口（TMAL）过程的keto-b-内酯的米德还原环化对四氢呋喃的反映选择性合成
8. SMOKE STUDIES OF SECONDARY FLOWS IN BENDS, TANDEM CASCADES AND HIGH-TURNING CONFIGURATIONS [R] . Arthur G. Hansen, Howard Z. Herzig, George R. Costello 1953

机译：本次二级流动的研究，TaNDEm级联和高转速配置

Progressive Studies on the Novel Samarium-Catalyzed Diastereoselective Tandem Semipinacol Rearrangement/Tishchenko Reduction of Secondary alpha-Hydroxy Epoxides

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