Transition-Metal-Free [3+2] Dehydration Cycloaddition of Donor-Acceptor Cyclopropanes With 2-Naphthols

Abstract

A Brønsted acid-catalyzed domino ring-opening cyclization transformation of donor-acceptor (D-A) cyclopropanes and 2-naphthols has been developed. This formal [3+2] cyclization reaction provided novel and efficient access to the naphthalene-fused cyclopentanes in the absence of any transition-metal catalysts or additives. This robust procedure was completed smoothly on a gram-scale to afford the corresponding product with comparable efficiency. Furthermore, the synthetic application of the prepared product has been demonstrated by its transformation into a variety of synthetically useful molecules.

Recent Advances in the Reactions of β-Naphthol at α-Position

“…Biju 课题组 [74] 报道了 TfOH 催化的醌单 缩醛(QMAs)与 β-萘酚的环加成反应构建萘并[1,1-b]呋 喃结构的方法. 2021 年, 翟宏斌课题组 [75] 也以 TfOH 作 为催化剂实现了 D-A 环丙烷和 β-萘酚的脱水[3＋2]环化 反应, 得到萘稠合的环戊烷, 该反应简单温和, 无过渡 金属参与, 底物范围广(Scheme 37).…”

Lewis acid triggered N-alkylation of sulfoximines through nucleophilic ring-opening of donor–acceptor cyclopropanes: synthesis of γ-sulfoximino malonic diesters

“…On the other hand, cyclopropane dicarboxylates 8 are simple and commercially available starting materials extensively used to synthesize natural products. The unique D–A characteristics of cyclopropane have made it a valuable component in a wide range of ring-opening, 9 cycloaddition, 10 and rearrangement reactions. 11 As a result, D–A cyclopropane has been studied for several decades and its applications in natural product synthesis, and heterocyclic and medicinal chemistry have been explored.…”