Details

Autor(en) / Beteiligte

• Huang, Ji‐Rong
• Sohail, Muhammad
• Taniguchi, Tohru
• Monde, Kenji
• Tanaka, Fujie

Titel

Formal (4+1) Cycloaddition and Enantioselective Michael–Henry Cascade Reactions To Synthesize Spiro[4,5]decanes and Spirooxindole Polycycles

Ist Teil von

• Angewandte Chemie International Edition, 2017-05, Vol.56 (21), p.5853-5857

Auflage

International ed. in English

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2017

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Spiro[4,5]decanes and polycyclic compounds bearing spiro[4,5]decane systems are important biofunctional molecules. Described are diastereoselective formal (4+1) cycloaddition reactions to afford oxindole‐functionalized spiro[4,5]decanes and organocatalytic enantioselective Michael–Henry cascade reactions of the (4+1) cycloaddition products to generate spirooxindole polycyclic derivatives bearing the spiro[4,5]decane system. Spiro[4,5]decanes bearing oxindoles containing three stereogenic centers and spirooxindole polycycles having seven stereogenic centers, including two all‐carbon chiral quaternary centers and one tetrasubstituted chiral carbon center, were obtained with high diastereo‐ and enantioselectivities. Spiro strategies: Strategies to construct oxindole‐functionalized spiro[4,5]decanes and polycyclic derivatives were developed. Through formal (4+1) cycloaddition and catalytic asymmetric Michael–Henry cascade reactions, products containing seven chiral centers, including two all‐carbon quaternary centers and one tetrasubstituted carbon center, were obtained with high diastereo‐ and enantioselectivities in two steps.