Enantioselective synthesis of (R)-2-cubylglycine including unprecedented rhodium mediated C–H insertion of cubane
Literature Information
Publication Date
2019-01-15
DOI
10.1039/C8OB02959H
Impact Factor
3.876
Authors
Sevan D. Houston, Benjamin A. Chalmers, G. Paul Savage, Craig M. Williams
View Original
Abstract
The first enantioselective synthesis of (R)-2-cubylglycine, an analogue of (R)-2-phenylglycine in which the phenyl ring has been replaced by cubane, is disclosed. The key step was a telescoped Strecker reaction using (S)-2-amino-2-phenylethanol as a chiral auxiliary. Exploration of an alternative synthetic approach resulted in unprecedented cubane C–H insertion.
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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
![(1S,4aR,5R,7S,7aS)-1-(beta-D-Glucopyranosyloxy)-5-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl alpha-D-galactopyranoside structure](https://static.chemtradehub.com/structs/817/81720-07-2-4ffd.webp "(1S,4aR,5R,7S,7aS)-1-(beta-D-Glucopyranosyloxy)-5-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl alpha-D-galactopyranoside structure")
(1S,4aR,5R,7S,7aS)-1-(beta-D-Glucopyranosyloxy)-5-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl alpha-D-galactopyranoside
CAS Number:
81720-07-2
Molecular Formula:
C21H34O14
3,3'-(Piperazine-1,4-diyl)bis(2-hydroxypropane-1-sulfonic acid) Sodium Salt
CAS Number:
108321-08-0
Molecular Formula:
C20H41N4Na3O16S4
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