Direct N-H/ N-Me Aziridination of Unactivated Olefins Using O-(Sulfonyl)hydroxylamines as Aminating Agents

Shekh Sabir; Chandra Bhan Pandey; Ajay K. Yadav; Bhoopendra Tiwari; Jawahar L. Jat

doi:10.1021/acs.joc.8b01673

Direct N-H/ N-Me Aziridination of Unactivated Olefins Using O-(Sulfonyl)hydroxylamines as Aminating Agents

Shekh Sabir, Chandra Bhan Pandey, Ajay K. Yadav, Bhoopendra Tiwari, Jawahar L. Jat

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

27 Citations (Scopus)

Abstract

Unactivated aziridines are the core substructures in a plethora of bioactive natural products and serve as building blocks in organic synthesis. Despite this, very limited methods are available to access them directly from olefins, as most of the known methods are devoted to their activated counterparts. Herein, we have developed a highly efficient Rh(II)-catalyzed method for the direct preparation of unactivated aziridines from olefins using O-(sulfonyl)hydroxylamines as the aminating agent. The reactions proceed with a high stereospecificity.

Original language	English
Pages (from-to)	12255-12260
Number of pages	6
Journal	The Journal of Organic Chemistry
Volume	83
Issue number	19
DOIs	https://doi.org/10.1021/acs.joc.8b01673
Publication status	Published - 5 Oct 2018
Externally published	Yes

Access to Document

10.1021/acs.joc.8b01673

Cite this

@article{037261b0380a42aea065c695cde66e67,

title = "Direct N-H/ N-Me Aziridination of Unactivated Olefins Using O-(Sulfonyl)hydroxylamines as Aminating Agents",

abstract = "Unactivated aziridines are the core substructures in a plethora of bioactive natural products and serve as building blocks in organic synthesis. Despite this, very limited methods are available to access them directly from olefins, as most of the known methods are devoted to their activated counterparts. Herein, we have developed a highly efficient Rh(II)-catalyzed method for the direct preparation of unactivated aziridines from olefins using O-(sulfonyl)hydroxylamines as the aminating agent. The reactions proceed with a high stereospecificity.",

author = "Shekh Sabir and Pandey, {Chandra Bhan} and Yadav, {Ajay K.} and Bhoopendra Tiwari and Jat, {Jawahar L.}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = oct,

day = "5",

doi = "10.1021/acs.joc.8b01673",

language = "English",

volume = "83",

pages = "12255--12260",

journal = "The Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Direct N-H/ N-Me Aziridination of Unactivated Olefins Using O-(Sulfonyl)hydroxylamines as Aminating Agents

AU - Sabir, Shekh

AU - Pandey, Chandra Bhan

AU - Yadav, Ajay K.

AU - Tiwari, Bhoopendra

AU - Jat, Jawahar L.

PY - 2018/10/5

Y1 - 2018/10/5

N2 - Unactivated aziridines are the core substructures in a plethora of bioactive natural products and serve as building blocks in organic synthesis. Despite this, very limited methods are available to access them directly from olefins, as most of the known methods are devoted to their activated counterparts. Herein, we have developed a highly efficient Rh(II)-catalyzed method for the direct preparation of unactivated aziridines from olefins using O-(sulfonyl)hydroxylamines as the aminating agent. The reactions proceed with a high stereospecificity.

AB - Unactivated aziridines are the core substructures in a plethora of bioactive natural products and serve as building blocks in organic synthesis. Despite this, very limited methods are available to access them directly from olefins, as most of the known methods are devoted to their activated counterparts. Herein, we have developed a highly efficient Rh(II)-catalyzed method for the direct preparation of unactivated aziridines from olefins using O-(sulfonyl)hydroxylamines as the aminating agent. The reactions proceed with a high stereospecificity.

UR - http://www.scopus.com/inward/record.url?scp=85053699753&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b01673

DO - 10.1021/acs.joc.8b01673

M3 - Article

C2 - 30192145

AN - SCOPUS:85053699753

SN - 0022-3263

VL - 83

SP - 12255

EP - 12260

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 19

ER -

Direct N-H/ N-Me Aziridination of Unactivated Olefins Using O-(Sulfonyl)hydroxylamines as Aminating Agents

Abstract

Access to Document

Other files and links

Cite this