Stereoselective Synthesis of 2,3,5-Trisubstituted Tetrahydrofurans Initiated by a Titanium-BINOLate-Catalyzed Vinylogous Aldol Reaction

被引：9

作者：

Hoffmeyer, Patrick ^{[1
]}

Schneider, Christoph ^{[1
]}

机构：

[1] Univ Leipzig, Inst Organ Chem, Johannisallee 29, D-04103 Leipzig, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 02期

关键词：

DIASTEREOSELECTIVE SYNTHESIS; PRINS CYCLIZATION; REAGENT;

D O I：

10.1021/acs.joc.8b02828

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of 2,3,5-trisubstituted tetrahydrofurans 3 has been achieved using a chiral titanium- BINOL complex as catalyst for the vinylogous Mukaiyama aldol reaction of bis(silyl) diendiolate 1 and an aldehyde. The ensuing BF3 center dot OEt2-mediated Prins-type cyclization with a second aldehyde gave rise to 2,3,5-substituted tetrahydrofurans 3 with generally good yields and excellent stereocontrol. In this process, three new sigma-bonds and three new stereogenic centers were generated in a one-pot process.

引用

页码：1079 / 1084

页数：6

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