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Asymmetric Photochemical Synthesis of Chiral 5‐( R )‐( l )‐Menthyloxy‐4‐Cycloaminobutyrolactones
Author(s) -
Wang ZhaoYang,
Jian TianYing,
Chen QingHua
Publication year - 2001
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20010190212
Subject(s) - chemistry , stereoselectivity , optically active , proton nmr , stereochemistry , enantioselective synthesis , medicinal chemistry , organic chemistry , catalysis
Through photocatalysed regiospecific and stereoselective additions of cycloamines to 5‐( R )‐( l )‐menthyloxy‐2 (5 H )‐furanone (3), chiral 5‐( R )‐( l )‐menthyloxy‐4‐cycloaminobutyrolactones were synthesized. In the new asymmetric photoaddition of compound 3, the N ‐methyl cyclic amines (4) gave novel chiral CC photoadducts (5) in 24–50% isolated yields with d. e . ≥ 98%. However, the secondary cyclic amines (6) afforded optically active NC photoadducts (7) in 34–58% isolated yields with d. e . ≥ 98% under the same condition. All the synthesized optically active compounds were identified on the basis of their analytical data and spectroscopic data, such as [α] 589 20 , IR, 1 H NMR, 13 C NMR, MS and elementary analysis. The photosynthesis of chiral butyrolactones and its mechanism were discussed in detail.