Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst

Takayuki Hoshi; Eisuke Ota; Yasuhide Inokuma; Junichiro Yamaguchi

doi:10.1021/acs.orglett.9b04048

Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst

Takayuki Hoshi, Eisuke Ota, Yasuhide Inokuma, Junichiro Yamaguchi^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

10 Citations (Scopus)

Abstract

A Rh-catalyzed asymmetric intramolecular Buchner ring expansion of α-alkyl-α-diazoesters has been developed. The present protocol generates a 5,7-fused ring system in an enantioselective manner while minimizing β-hydrogen migration, which has been a competing reaction when using α-alkyl-α-diazoesters. The ester functionality at the bridgehead position would be a useful synthetic handle for further derivatization to complex molecules including natural products.

Original language	English
Pages (from-to)	10081-10084
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.9b04048
Publication status	Published - 2019 Dec 20

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b04048

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title = "Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst",

abstract = "A Rh-catalyzed asymmetric intramolecular Buchner ring expansion of α-alkyl-α-diazoesters has been developed. The present protocol generates a 5,7-fused ring system in an enantioselective manner while minimizing β-hydrogen migration, which has been a competing reaction when using α-alkyl-α-diazoesters. The ester functionality at the bridgehead position would be a useful synthetic handle for further derivatization to complex molecules including natural products.",

author = "Takayuki Hoshi and Eisuke Ota and Yasuhide Inokuma and Junichiro Yamaguchi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant No. JP19H02726, JP18H04272 (to J.Y.). We thank Mr. Yumehiro Manabe (Hokkaido University) for his support of single-crystal X-ray analysis. The Materials Characterization Central Laboratory at Waseda University is acknowledged for HRMS measurement. Funding Information: This work was supported by JSPS KAKENHI Grant No. JP19H02726, JP18H04272 (to J.Y.). We thank Mr. Yumehiro Manabe (Hokkaido University) for his support of single-crystal X-ray analysis. The Materials Characterization Central Laboratory at Waseda University is acknowledged for HRMS measurement. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.9b04048",

language = "English",

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T1 - Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst

AU - Hoshi, Takayuki

AU - Ota, Eisuke

AU - Inokuma, Yasuhide

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant No. JP19H02726, JP18H04272 (to J.Y.). We thank Mr. Yumehiro Manabe (Hokkaido University) for his support of single-crystal X-ray analysis. The Materials Characterization Central Laboratory at Waseda University is acknowledged for HRMS measurement. Funding Information: This work was supported by JSPS KAKENHI Grant No. JP19H02726, JP18H04272 (to J.Y.). We thank Mr. Yumehiro Manabe (Hokkaido University) for his support of single-crystal X-ray analysis. The Materials Characterization Central Laboratory at Waseda University is acknowledged for HRMS measurement. Publisher Copyright: Copyright © 2019 American Chemical Society.

PY - 2019/12/20

Y1 - 2019/12/20

N2 - A Rh-catalyzed asymmetric intramolecular Buchner ring expansion of α-alkyl-α-diazoesters has been developed. The present protocol generates a 5,7-fused ring system in an enantioselective manner while minimizing β-hydrogen migration, which has been a competing reaction when using α-alkyl-α-diazoesters. The ester functionality at the bridgehead position would be a useful synthetic handle for further derivatization to complex molecules including natural products.

AB - A Rh-catalyzed asymmetric intramolecular Buchner ring expansion of α-alkyl-α-diazoesters has been developed. The present protocol generates a 5,7-fused ring system in an enantioselective manner while minimizing β-hydrogen migration, which has been a competing reaction when using α-alkyl-α-diazoesters. The ester functionality at the bridgehead position would be a useful synthetic handle for further derivatization to complex molecules including natural products.

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Asymmetric Synthesis of a 5,7-Fused Ring System Enabled by an Intramolecular Buchner Reaction with Chiral Rhodium Catalyst

Abstract

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