Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

Zhurakovskyi, Oleksandr; Türkmen, Yunus E.; Löffler, Lorenz E.; Moorthie, Vijayalakshmi A.; Chen, C. Chun; Shaw, Michael; Crimmin, Mark R.; Ferrara, Marco; Ahmad, Mushtaq; Ostovar, Mehrnoosh; Matlock, Johnathan V.; Aggarwal, Varinder K.

doi:10.1002/ange.201712065

Cited by 6 publications

(1 citation statement)

References 46 publications

(19 reference statements)

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“…As shown in Fig. 2, chiral sulfur ylides might serve as a one-carbon unit to be introduced through asymmetric aziridination [50][51][52][53][54][55] . Subsequent rearrangement might be promoted by a Brønsted or Lewis acid to redevelop the aromaticity and complete the formal enantioselective one-carbon insertion.…”

Section: Resultsmentioning

confidence: 99%

Conversion of anilines to chiral benzylic amines via formal one-carbon insertion into aromatic C–N bonds

Yang

et al. 2020

Nat Commun

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Insertion of atoms into aromatic carbon-nitrogen bonds is an appealing method for the synthesis of nitrogen-containing molecules and it has the advantage of the availability and abundance of anilines. However, the direct cleavage of aromatic carbon-nitrogen bonds is challenging due to the particularly inert and stable nature of these bonds. Here we report a formal, enantioselective one-carbon insertion into an aromatic carbon-nitrogen bond via an aromaticity dissembly-reconstruction process to directly convert anilines to chiral α-branched benzylic amines. The process involves oxidative dearomatization of para-substituted anilines, chiral sulfur ylide-mediated asymmetric aziridination, and subsequent rearrangement. Chiral sulfur ylides serve as one-carbon insertion units.

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Section: Resultsmentioning

confidence: 99%

Conversion of anilines to chiral benzylic amines via formal one-carbon insertion into aromatic C–N bonds

Yang

et al. 2020

Nat Commun

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A Ten‐Step Total Synthesis of Speradine C

et al. 2019

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A Ten‐Step Total Synthesis of Speradine C

et al. 2019

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The first total synthesis of speradine Ch as been achieved in only ten steps from ac ommercially available 4bromoindole.Salient features of the work are the formation of four rings through three cyclizations,n amely ab ioinspired [3+ +2] annulation to form the C/D rings,a nN CS-mediated oxidation to construct the Ering, and aR u-catalyzed ketohydroxylation to assemble the Fring. This work highlights how strategic ring constructions can streamline the synthesis of polycyclic compounds. Scheme 1. Retrosynthetic analysis of speradine C.Scheme 2. Synthesis of tetracycle 9.THF = tetrahydrofuran, DMF = N,N-dimethylformamide, Tf = trifluoromethanesulfonyl, LiHMDS = lithium hexamethyldisilazide.Scheme 3. Proposed mechanism for the formation of 9a-c.

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Enantioselective Synthesis of the Cyclopiazonic Acid Family Using Sulfur Ylides

Cited by 6 publications

References 46 publications

Conversion of anilines to chiral benzylic amines via formal one-carbon insertion into aromatic C–N bonds

Conversion of anilines to chiral benzylic amines via formal one-carbon insertion into aromatic C–N bonds

A Ten‐Step Total Synthesis of Speradine C

A Ten‐Step Total Synthesis of Speradine C

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