Stereodivergent Synthesis of Functionalized Tetrahydropyrans Accelerated by Mechanism-Based Allylboration and Bioinspired Oxa-Michael Cyclization

被引：24

作者：

Yang, Lin ^{[1
]}

Lin, Zuming ^{[1
]}

Huang, Sha-Hua ^{[1
,2
]}

Hong, Ran ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, CAS Key Lab Synthet Chem Nat Subst, 345 Lingling Rd, Shanghai 200032, Peoples R China

[2] Shanghai Inst Technol, Sch Chem & Environm Engn, 100 Haiquan Rd, Shanghai 201418, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 21期

基金：

中国国家自然科学基金;

关键词：

allenes; boranes; heterocycles; homoallylic alcohols; Michael addition; NATURAL-PRODUCT SYNTHESIS; A STRUCTURAL REVISION; GENE-CLUSTER; LASONOLIDE-A; STEREOSELECTIVE-SYNTHESIS; GEOMETRIC ISOMERS; BIOSYNTHESIS; ALDEHYDES; (+)-LASONOLIDE-A; (-)-LASONOLIDE;

D O I：

10.1002/anie.201600558

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A stereodivergent strategy enabled by bioinspired oxa-Michael cyclization was developed for the synthesis of functionalized tetrahydropyrans on the basis of the inherent symmetry in 1,3-diols, the symmetries of which were tunable by stereoselective hydroboration of an allene with a variety of alkylborane reagents and subsequent allylation of an aldehyde. The mechanism-based utilization of monoalkyl borane in the hydroboration and allylation cascade is unprecedented.

引用

页码：6280 / 6284

页数：5

共 13 条

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Gutierrez-Marquez, Ricardo A.
Garcia-Ramirez, Jazmin
Silva, Ana L.
Miranda, Luis D.
TETRAHEDRON LETTERS, 2024, 147
[2] Concise Synthesis of Tetrahydropyrans by a Tandem Oxa-Michael/Tsuji-Trost Reaction
Wang, Liang
Li, Pengfei
Menche, Dirk
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (48) : 9270 - 9273
[3] Tandem Nucleophilic Addition/Oxa-Michael Reaction for the Synthesis of cis-2,6-Disubstituted Tetrahydropyrans
Gharpure, Santosh J.
Prasad, J. V. K.
Bera, Kalisankar
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (17) : 3570 - 3574
[4] Stereoselective Synthesis of Tetrahydropyrans through Tandem and Organocatalytic Oxa-Michael Reactions: Synthesis of the Tetrahydropyran Cores of ent-(+)-Sorangicin A
Lee, Kiyoun
Kim, Hyoungsu
Hong, Jiyong
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (05) : 1025 - 1032
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Eastman, Harry
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O'Reilly, Elaine
CHEMCATCHEM, 2019, 11 (16) : 3760 - 3762
[6] Synthesis of Multisubstituted Indanedione Based Spiropyrans via Oxa-Michael/Michael Cascade Reaction
Reddy, Yeruva Pavankumar
Gudise, Veera Babu
Settipalli, Poorna Chandrasekhar
Anwar, Shaik
CHEMISTRYSELECT, 2021, 6 (18): : 4456 - 4460
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ORGANIC LETTERS, 2012, 14 (18) : 4758 - 4761
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Kim, Hyoungsu
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (41) : 7577 - 7581
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CHEMICAL SCIENCE, 2017, 8 (01) : 482 - 490
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ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (08) : 1277 - 1286

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