Enantioselective Dearomatization of Indoles by an Azoalkene‐Enabled (3+2) Reaction: Access to Pyrroloindolines

• Published in: Angewandte Chemie International Edition Vol. 59; no. 2; pp. 648 - 652
• Main Authors: Mei, Guang‐Jian, Tang, Xiwen, Tasdan, Yildiz, Lu, Yixin
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 07.01.2020; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Chemistry; Chemistry, Multidisciplinary; dearomatization; Enantiomers; enantioselectivity; heterocylces; Indoles; organocatalysis; Physical Sciences; Science & Technology; Substrates; synthetic methods; enantioselectivity; ANNULATION; dearomatization; CATIONS; organocatalysis; CYCLOADDITION; QUATERNARY STEREOGENIC CENTERS; PHOSPHORIC-ACID; heterocylces; DIELS-ALDER REACTION; CONSTRUCTION; RECENT PROGRESS; CATALYTIC ASYMMETRIC-SYNTHESIS; synthetic methods; N-SULFONYLAZIRIDINES
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201911686

The enantioselective dearomatization of indoles by an organocatalytic (3+2) reaction has been established. The reaction makes use of simple indole derivatives as substrates, and employs azoalkenes reaction partners. A wide range of pyrroloindolines containing an all‐carbon quaternary stereogenic center were readily prepared in high yields and with excellent enantioselectivities. That simple: The enantioselective dearomatization of indoles by an organocatalytic (3+2) reaction has been established. The reaction makes use of simple indole derivatives as substrates and azoalkenes as 1,3‐diople reaction partners. A wide range of pyrroloindolines containing an all‐carbon quaternary stereogenic center were readily prepared in high yields and with excellent enantioselectivity.