Universität zu Köln

Ullrich, Patrick, Schmauck, Julie, Brauns, Marcus, Mantel, Marvin ORCID: 0000-0002-3541-3388, Breugst, Martin ORCID: 0000-0003-0950-8858 and Pietruszka, Jorg ORCID: 0000-0002-9819-889X (2020). Enantioselective Allylation of Indoles: A Surprising Diastereoselectivity. J. Org. Chem., 85 (4). S. 1894 - 1906. WASHINGTON: AMER CHEMICAL SOC. ISSN 1520-6904

Full text not available from this repository.

Abstract

Herein we show a novel approach toward the allylation of indoles. Thereby, we explore a class of bench-stable allylboronates and fine-tune their reactivity. The allylations of different substituted indoles proceed with negligible diastereo- and excellent enantioselectivities. This surprising selectivity (up to 99:1 er, up to approximate to 60:40 dr) is rationalized by DFT calculations.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Ullrich, Patrick UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmauck, Julie UNSPECIFIED UNSPECIFIED UNSPECIFIED Brauns, Marcus UNSPECIFIED UNSPECIFIED UNSPECIFIED Mantel, Marvin UNSPECIFIED orcid.org/0000-0002-3541-3388 UNSPECIFIED Breugst, Martin UNSPECIFIED orcid.org/0000-0003-0950-8858 UNSPECIFIED Pietruszka, Jorg UNSPECIFIED orcid.org/0000-0002-9819-889X UNSPECIFIED
URN:	urn:nbn:de:hbz:38-344253
DOI:	10.1021/acs.joc.9b02573
Journal or Publication Title:	J. Org. Chem.
Volume:	85
Number:	4
Page Range:	S. 1894 - 1906
Date:	2020
Publisher:	AMER CHEMICAL SOC
Place of Publication:	WASHINGTON
ISSN:	1520-6904
Language:	English
Faculty:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language CATALYZED ASYMMETRIC HYDROGENATION; MAIN-GROUP THERMOCHEMISTRY; CARBONYL-COMPOUNDS; ALDEHYDES; ALLYLBORATION; IMINES; LEWIS; ACID; ADDITIONS; KINETICS Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/34425