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

7 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

Access to Document

10.1021/acs.orglett.9b04048

Cite this

@article{9f02bbb6459746f09e86e2fb023d6fd3,

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.",

year = "2019",

month = dec,

day = "20",

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

language = "English",

volume = "21",

pages = "10081--10084",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "24",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=85076736761&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85076736761&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.9b04048

DO - 10.1021/acs.orglett.9b04048

M3 - Article

C2 - 31808701

AN - SCOPUS:85076736761

VL - 21

SP - 10081

EP - 10084

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 24

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this