From Enantiopure Hydroxyaldehydes to Complex Heterocyclic Scaffolds: Development of Domino Petasis/Diels-Alder and Cross-Metathesis/Michael Addition Reactions

被引：21

作者：

Cannillo, Alexandre ^{[1
]}

Norsikian, Stephanie ^{[1
]}

Dau, Marie-Elise Tran Huu ^{[1
]}

Retailleau, Pascal ^{[1
]}

Iorga, Bogdan I. ^{[1
]}

Beau, Jean-Marie ^{[1
,2
,3
]}

机构：

[1] CNRS, UPR 2301, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France

[2] Univ Paris 11, F-91405 Orsay, France

[3] CNRS, Lab Synth Biomol, Inst Chim Mol & Mat Orsay, F-91405 Orsay, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 38期

关键词：

borono-Mannich reaction; carbohydrates; Diels-Alder reaction; domino reactions; metathesis; BORONO-MANNICH REACTION; ASYMMETRIC-SYNTHESIS; SELECTIVE OXIDATION; ORGANOBORONIC ACIDS; EFFICIENT APPROACH; CONCISE SYNTHESIS; FORMAL SYNTHESIS; DIELS; ALCOHOLS; STEREOSELECTIVITY;

D O I：

10.1002/chem.201402965

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

One-step assembly of hexahydroisoindole scaffolds by a sequence that combines the Petasis (borono-Mannich) and Diels-Alder reactions is described. The unique selectivity observed experimentally was confirmed by quantum calculations. The current method is applicable to a broad range of substrates, including free sugars, and holds significant potential to efficiently and stereoselectively build new heterocyclic structures. This easy and fast entry to functionalized polycyclic compounds can be pursued by further transformations, for example, additional ring closure by a cross-metathesis/Michael addition domino sequence.

引用

页码：12133 / 12143

页数：11

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