Intramolecular asymmetric oxidopyrylium-based [5+2] cycloadditions

被引：5

作者：

Rokey, Samantha N. ^{[1
]}

Simanis, Justin A. ^{[1
]}

Law, Chunyin M. ^{[1
]}

Pohani, Shilpa ^{[1
]}

Behrends, Samantha Willens ^{[1
]}

Bulandr, Jacob J. ^{[1
]}

Ferrence, Gregory M. ^{[1
]}

Goodell, John R. ^{[1
]}

Mitchell, T. Andrew ^{[1
]}

机构：

[1] Illinois State Univ, Dept Chem, Campus Box 4160, Normal, IL 61790 USA

来源：

TETRAHEDRON LETTERS | 2020年 / 61卷 / 41期

基金：

美国国家科学基金会;

关键词：

5+2] cycloadditions; Chiral auxiliary; Asymmetric; Organic synthesis; PYRONE-ALKENE CYCLOADDITIONS; PROLINOL ETHER ENAMINES; NATURAL-PRODUCTS; TUMOR PROMOTERS; REACTIVITY; ORGANOCATALYSIS; SELECTIVITY; STRATEGIES; STABILITY; CATALYSIS;

D O I：

10.1016/j.tetlet.2020.152377

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular oxidopyrylium-based [5 + 2] cycloadditions utilizing chiral auxiliaries were investigated. Both acetoxypyranones and silyloxypyrones were employed and sulfinimines, oxazolidinones, hydrazones, and chiral enamines were explored. Carbonyl-based auxiliaries gave low selectivity, but enamines afforded excellent diastereoselectivity. Overall, facial selectivity varied significantly providing insight regarding the scope and limitation of chiral auxiliary-based oxidopyrylium-alkene [5 + 2] cycloadditions. (C) 2020 Elsevier Ltd. All rights reserved.

引用

页数：5

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