Highly Diastereoselective Multicomponent Cascade Reactions: Efficient Synthesis of Functionalized 1-Indanols

• Published in: Angewandte Chemie International Edition Vol. 52; no. 5; pp. 1539 - 1542
• Main Authors: Jiang, Jun, Guan, Xiaoyu, Liu, Shunying, Ren, Baiyan, Ma, Xiaochu, Guo, Xin, Lv, Fengping, Wu, Xiang, Hu, Wenhao
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 28.01.2013; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Alcohols - chemistry; Aldehydes - chemistry; Benzofurans - chemistry; Carbon; cascade reactions; Cascades; Catalysis; Chemistry; Chemistry, Multidisciplinary; Crystallography, X-Ray; Derivatives; diastereoselectivity; Formations; Molecular Conformation; multicomponent reactions; oxonium ylides; Oxygen - chemistry; Physical Sciences; Science & Technology; stereogenic centers; Stereoisomerism; Synthesis; Trapping; multicomponent reactions; ASYMMETRIC-SYNTHESIS; MOLECULAR COMPLEXITY; diastereoselectivity; CHIRAL BRONSTED ACID-RH-2(OAC); O-H INSERTION; oxonium ylides; ARYL DIAZOACETATES; cascade reactions; COOPERATIVE CATALYSIS; COLEOPHOMONE-B; ENANTIOSELECTIVE 3-COMPONENT REACTIONS; DOMINO MICHAEL-ALDOL; STEREOSELECTIVE-SYNTHESIS; stereogenic centers
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201208391

Trapped: A Michael‐aldol‐type cascade reaction including the trapping of an oxonium ylide through a delayed proton shift leads to the formation of multiple stereocenters in a mild one‐pot synthesis. Enantiomerically pure indanol derivatives with four stereocenters and a stereogenic quaternary carbon center were easily obtained through this method in moderate to good yields.