期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 352, 期 11-12, 页码 2011-2022出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000189
关键词
asymmetric catalysis; asymmetric synthesis; diastereoselectivity; enantioselectivity; heterocyclic dienoxy silanes; vinylogous aldol reaction
资金
- Universita degh Studi di Parma
Denmark's chiral bisphosphoramide/silicon tetrachloride system performs as an excellent Lewis base-Lewis acid catalyst for the vmylogous Mukaiyama aldol reaction of pyrrole- and furan-based dienoxy silanes with aromatic and heteroaromatic aldehydes. This asymmetric methodology provides a powerful synthetic entry to a variety of delta-hydroxylated gamma-butenolide-type frameworks with high efficiency and valuable margins of regio-. diastereo-, and enantioselectivity. Notably, the nature of the heteroatom within the vinylogous dienoxy silane donor heavily impacts the diastereocontrol. with syn-configured aldol adducts emerging from pyrroles bearing electron-withdrawing N-protecting groups (Boc, Ts. and Cbz) and anti-con figured adducts prevailing when furan- or N-alkyl/alkenylpyrrole donors are involved.
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