title: cis-2,3-Disubstituted cyclopropane 1,1-diesters in [3 + 2] annulations with aldehydes: highly diastereoselective construction of densely substituted tetrahydrofurans.
abstract: A series of cis-2,3-disubstituted cyclopropane 1,1-diesters were examined in the AlCl3-promoted [3 + 2]-annulations with aldehydes. In this reaction, these cis-cyclopropanes displayed reactivities starkly different from their trans counterparts in terms of the high chemical yields (up to 98%) and provided the desired annulation products with excellent diastereomeric purity. This protocol provides a facile and highly stereoselective way to construct synthetically useful pentasubstituted tetrahydrofurans not easily accessible using other methods.
authors: Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Institute of Organic Chemistry, College of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China. gshyang@mail.ahnu.edu.cn
authors: Gaosheng
authors: G
authors: Yang
authors: Yongxian
authors: Y
authors: Sun
authors: Yue
authors: Y
authors: Shen
authors: Zhuo
authors: Z
authors: Chai
authors: Shuangliu
authors: S
authors: Zhou
authors: Jiang
authors: J
authors: Chu
authors: Jun
authors: J
authors: Chai
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D003521:Cyclopropanes / Q000737:chemistry*; D004952:Esters; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D003521:Cyclopropanes; D004952:Esters; D005663:Furans