Copper-mediated aerobic synthesis of 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles from N-allyl/propargyl enamine carboxylates

Kah Kah Toh; Yi Feng Wang; Eileen Pei Jian Ng; Shunsuke Chiba

doi:10.1021/ja206580j

Copper-mediated aerobic synthesis of 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles from N-allyl/propargyl enamine carboxylates

Kah Kah Toh, Yi Feng Wang, Eileen Pei Jian Ng, Shunsuke Chiba^*

^*Corresponding author for this work

Nanyang Technological University

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

194 Citations (Scopus)

Abstract

Synthetic methods for 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O ₂ atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.

Original language	English
Pages (from-to)	13942-13945
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	35
DOIs	https://doi.org/10.1021/ja206580j
Publication status	Published - Sept 7 2011
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja206580j

Cite this

@article{bee3a5cde8b14e49b997cd547952df98,

title = "Copper-mediated aerobic synthesis of 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles from N-allyl/propargyl enamine carboxylates",

abstract = "Synthetic methods for 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O 2 atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.",

author = "Toh, {Kah Kah} and Wang, {Yi Feng} and Ng, {Eileen Pei Jian} and Shunsuke Chiba",

year = "2011",

month = sep,

day = "7",

doi = "10.1021/ja206580j",

language = "English",

volume = "133",

pages = "13942--13945",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "35",

}

TY - JOUR

T1 - Copper-mediated aerobic synthesis of 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles from N-allyl/propargyl enamine carboxylates

AU - Toh, Kah Kah

AU - Wang, Yi Feng

AU - Ng, Eileen Pei Jian

AU - Chiba, Shunsuke

PY - 2011/9/7

Y1 - 2011/9/7

N2 - Synthetic methods for 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O 2 atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.

AB - Synthetic methods for 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O 2 atmosphere and involve intramolecular cyclopropanation and carbooxygenation, respectively. These methodologies take advantage of orthogonal modes of chemical reactivity of readily available N-allyl/propargyl enamine carboxylates; the complementary pathways can be accessed by slight modification of the reaction conditions.

UR - http://www.scopus.com/inward/record.url?scp=80052306516&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80052306516&partnerID=8YFLogxK

U2 - 10.1021/ja206580j

DO - 10.1021/ja206580j

M3 - Article

C2 - 21823614

AN - SCOPUS:80052306516

SN - 0002-7863

VL - 133

SP - 13942

EP - 13945

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 35

ER -

Copper-mediated aerobic synthesis of 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles from N-allyl/propargyl enamine carboxylates

Abstract

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this