期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 355, 期 13, 页码 2499-2505出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300392
关键词
asymmetric allylation; butyrolactones; chiral phosphoric acids; hydroxymatairesinol; organozinc reagents
资金
- SNIC through Uppsala Multidisciplinary Center for Advanced Computational Science (UPPMAX) [p2011197]
- Austrian Science Fund (FWF) [J3193-N17]
Asymmetric allylation of (hetero)aromatic aldehydes by a zinc(II)-allylbutyrolactone species catalyzed by a chiral BINOL-type phosphoric acid gave beta-substituted alpha-methylenebutyrolactones in 68 to >99% ee and 52-91% isolated yield. DFT studies on the intermediate Zn2+-complex - crucial for chiral induction - suggest a six-membered ring intermediate, which allows the phosphoric acid moiety to activate the aldehyde. The methodology was applied to the synthesis of the antitumour natural product (S)-(-)-hydroxymatairesinol.
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