2-(3'-Chlorobiphenyl-3-yl)-4,6-diphenyl-1,3,5-triazine
CAS Number:
1443049-83-9
Molecular Formula:
C27H18ClN3
Brønsted-base-catalyzed remote cascade reactivity of 2,4-dienones – asymmetric synthesis of tetrahydrothiophenes
Literature Information
Publication Date
2017-10-04
DOI
10.1039/C7OB02397A
Impact Factor
3.876
Authors
Artur Przydacz, Rafał Kowalczyk, Łukasz Albrecht
View Original
Abstract
This study demonstrates that the remote cascade functionalization of 2,4-dienones can be realized by employing Brønsted base catalysis. The developed cascade involving 1,6-addition followed by the intramolecular aldol reaction provides a straightforward access to polysubstituted tetrahydrothiophene derivatives of biological and synthetic importance. Target products, bearing three contiguous stereocenters including one quaternary, have been obtained with excellent yields (up to 98%) and with good to high stereocontrol (>20 : 1 dr, up to 97 : 3 er) with the reaction cascade being promoted by a simple and readily available cinchona alkaloid cinchonine.
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Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
2-Chloro-4-nitrophenyl 6-deoxy-alpha-L-galactopyranoside
CAS Number:
157843-41-9
Molecular Formula:
C12H14ClNO7
5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
CAS Number:
32602-81-6
Molecular Formula:
C27H30O15
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