6533b860fe1ef96bd12c3a59

RESEARCH PRODUCT

Organocatalytic Domino Oxa-Michael/1,6-Addition Reactions: Asymmetric Synthesis of Chromans Bearing Oxindole Scaffolds.

Arto ValkonenDieter EndersKun ZhaoKari RissanenYing ZhiTao Shu

subject

chromansAddition reaction010405 organic chemistrydomino reactionspara-quinone methidesEnantioselective synthesisGeneral MedicineGeneral Chemistry010402 general chemistry01 natural sciencesoxa-Michael additionCatalysisDomino0104 chemical sciencesStereocenterchemistry.chemical_compoundchemistryCascade reactionOrganocatalysisOrganic chemistryorganocatalysisOxindoleBifunctionalta116

description

An asymmetric organocatalytic domino oxa-Michael/1,6-addition reaction of ortho-hydroxyphenyl-substituted para-quinone methides and isatin-derived enoates has been developed. In the presence of 5 mol % of a bifunctional thiourea organocatalyst, this scalable domino reaction affords 4-phenyl-substituted chromans bearing spiro-connected oxindole scaffolds and three adjacent stereogenic centers in good to excellent yields (up to 98 %) and with very high stereoselectivities (up to >20:1 d.r., >99 % ee).

yearjournalcountryeditionlanguage
2016-09-07Angewandte Chemie (International ed. in English)
10.1002/anie.201606947https://pubmed.ncbi.nlm.nih.gov/27600477