由乙炔气体和酮合成非对映异构体纯的、很少官能化的烯酰基二氢吡喃、1,6-二酮和环戊烷。

Diastereomerically pure rarely functionalized alkenoyl dihydropyrans, 1,6-diketones, and cyclopentanes from acetylene gas and ketones.

机构信息

A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences 1 Favorsky Str., 664033 Irkutsk, Russia.

出版信息

Org Biomol Chem. 2022 Aug 24;20(33):6593-6605. doi: 10.1039/d2ob01068b.

DOI:10.1039/d2ob01068b

PMID:35920307

Abstract

Pure ()-alkenoyl dihydropyrans are stereoselectively assembled from 2-acetyl-3,4-dihydropyrans (products of one-pot self-organization of acetylene gas and ketones) and aromatic aldehydes (52-86% yields). Furthermore, ()-alkenoyl dihydropyrans undergo ring opening (acid hydrolysis) to afford 5-hydroxy-1,6-diketones (44-67% yields) and acetyl-2-()-styryl-2,3-dihydroxycyclopentanes (19-32% yields), both as single diastereomers.

摘要

纯（）-烯酰基二氢吡喃可从 2-乙酰基-3,4-二氢吡喃（乙炔气体和酮一锅自组织的产物）和芳香醛（52-86%产率）立体选择性地组装得到。此外，（）-烯酰基二氢吡喃开环（酸水解）得到 5-羟基-1,6-二酮（44-67%产率）和乙酰基-2-（）-苯乙烯基-2,3-二羟基环戊烷（19-32%产率），两者均为单一非对映异构体。