Asymmetric Photochemical Synthesis of Chiral 5-(R)-(l)-Men-thyloxy-4-Cycloaminobutyrolactones

• 来源期刊: 中国化学（英文版）
• 学科: 化学
• 年，卷（期）: 2001,（2）
• 页码范围: 177-183
• 页数: 7页
• 分类号: O6
• 语种: 英文

摘要

Tnrough photocatalysed regiospecific and stereoselective addi-tions of cycloamines to 5-(R)-(l)-menthyloxy-2(5H)-fura-none(3),chiral5-(R)-(l)-menthyloxy-4-cycloaminobuty-rolactones were synthesized,In the new asymmetric photoad-dition of compound 3, the N-methyl cyclic amines (4) gave novel chiral C—C photoadducts (5)in 24-50% isolated yields withd.e.≥98%.However,the secondary cyclic amines (6)afforded optically active N-C photoadducts(7)in 34-58% inolated yields with d.e≥98% under the same condition.All the synthesized optically active compoumds were identified on the basis of their analytical data and spectroscop-ic data,such as [α]20 589,IR, 1HNMR,13CNMR,MS and el-ementary analysis.The photosynthesis of chiral butyrolacctones and its mechanism were discussed in detail.