An Efficient Stereoselective Synthesis of cis-2,6-Disubstituted Tetrahydropyrans via Gold-Catalyzed Meyer-Schuster Rearrangement/Hydration/oxa-Michael Addition Sequence

被引：1

作者：

Morita, Nobuyoshi ^{[1
]}

Yamashita, Daichi ^{[1
]}

Hashimoto, Yoshimitsu ^{[1
]}

Tamura, Osamu ^{[1
]}

机构：

[1] Showa Pharmaceut Univ, Dept Pharm, 3-3165 Higashi Tamagawagakuen, Machida, Tokyo 1948543, Japan

来源：

CATALYSTS | 2024年 / 14卷 / 04期

关键词：

gold catalyst; Meyer-Schuster rearrangement; hydration; oxa-Michael addition; 2,6-disubstituted tetrahydropyrans; GOLD(I)/(III)-CATALYZED SYNTHESIS; CYCLIC ETHERS; MARINE; CONSTRUCTION; PHORBOXAZOLE; MACROLIDES;

D O I：

10.3390/catal14040228

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An efficient stereoselective synthesis of cis-2,6-disubstituted tetrahydropyrans <bold>14a</bold>-<bold>c</bold> has been achieved via gold-catalyzed Meyer-Schuster rearrangement/hydration/oxa-Michael addition sequence from bis-propargylic alcohols <bold>13a</bold>-<bold>c</bold>. The reaction of <bold>13a</bold> proceeds via 2,6-disubstituted tetrahydropyran <bold>14 ' a</bold> as an intermediate.

引用

页数：12

共 7 条

[1] 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
[2] 2,6-Disubstituted Tetrahydropyrans by Domino Meyer-Schuster Rearrangement-Hetero-Michael Addition of 6-Alkyne-1,5-diols
Wohland, Max
Maier, Martin E.
SYNLETT, 2011, (11) : 1523 - 1526
[3] Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via an intramolecular bismuth-mediated oxa-conjugate addition reaction
Evans, PA
Andrews, WJ
TETRAHEDRON LETTERS, 2005, 46 (34) : 5625 - 5627
[4] A General Procedure for the Synthesis of Enones via Gold-Catalyzed Meyer-Schuster Rearrangement of Propargylic Alcohols at Room Temperature
Pennell, Matthew N.
Unthank, Matthew G.
Turner, Peter
Sheppard, Tom D.
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (05): : 1479 - 1482
[5] Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via the reductive etherification of δ-trialkylsilyloxy substituted ketones:: Total synthesis of (-)-centrolobine
Evans, PA
Cui, J
Gharpure, SJ
ORGANIC LETTERS, 2003, 5 (21) : 3883 - 3885
[6] Enantioselective Synthesis of 2,6-cis-Disubstituted Tetrahydropyrans via a Tandem Catalytic Asymmetric Hydrogenation/Oxa-Michael Cyclization: An Efficient Approach to (-)-Centrolobine
Xie, Jian-Hua
Guo, Lu-Chuan
Yang, Xiao-Hui
Wang, Li-Xin
Zhou, Qi-Lin
ORGANIC LETTERS, 2012, 14 (18) : 4758 - 4761
[7] Gold Meets Rhodium: Tandem One-Pot Synthesis of β-Disubstituted Ketones via Meyer-Schuster Rearrangement and Asymmetric 1,4-Addition
Hansmann, Max M.
Hashmi, A. Stephen K.
Lautens, Mark
ORGANIC LETTERS, 2013, 15 (13) : 3226 - 3229

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