Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives

Anthony Cohen; Yogesh Siddaraju; Ilan Marek

doi:10.1021/acs.orglett.2c03305

Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives

Anthony Cohen, Yogesh Siddaraju, Ilan Marek

Chemistry

Technion - Israel Institute of Technology

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

Abstract

We report the directed diastereoselective Simmons-Smith cyclopropanation and vanadium-catalyzed epoxidation reactions of alkenyl cyclopropyl carbinol derivatives. The reaction furnished densely substituted stereodefined bicyclopropanes and cyclopropyl oxiranes as a single diastereomer in each case. The remarkable selectivity is obtained thanks to the rigidity of the cyclopropyl core, allowing diastereoselective reactions on the alkenyl moiety. This emphasizes the uniqueness of the cyclopropyl ring as a central platform in stereoselective synthesis.

Original language	English
Pages (from-to)	8322-8325
Number of pages	4
Journal	Organic Letters
Volume	24
Issue number	45
DOIs	https://doi.org/10.1021/acs.orglett.2c03305
State	Published - 18 Nov 2022

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.2c03305

Cite this

@article{a82756876978434aaa28d256a552198b,

title = "Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives",

abstract = "We report the directed diastereoselective Simmons-Smith cyclopropanation and vanadium-catalyzed epoxidation reactions of alkenyl cyclopropyl carbinol derivatives. The reaction furnished densely substituted stereodefined bicyclopropanes and cyclopropyl oxiranes as a single diastereomer in each case. The remarkable selectivity is obtained thanks to the rigidity of the cyclopropyl core, allowing diastereoselective reactions on the alkenyl moiety. This emphasizes the uniqueness of the cyclopropyl ring as a central platform in stereoselective synthesis.",

author = "Anthony Cohen and Yogesh Siddaraju and Ilan Marek",

year = "2022",

month = nov,

day = "18",

doi = "10.1021/acs.orglett.2c03305",

language = "الإنجليزيّة",

volume = "24",

pages = "8322--8325",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "45",

}

TY - JOUR

T1 - Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives

AU - Cohen, Anthony

AU - Siddaraju, Yogesh

AU - Marek, Ilan

PY - 2022/11/18

Y1 - 2022/11/18

N2 - We report the directed diastereoselective Simmons-Smith cyclopropanation and vanadium-catalyzed epoxidation reactions of alkenyl cyclopropyl carbinol derivatives. The reaction furnished densely substituted stereodefined bicyclopropanes and cyclopropyl oxiranes as a single diastereomer in each case. The remarkable selectivity is obtained thanks to the rigidity of the cyclopropyl core, allowing diastereoselective reactions on the alkenyl moiety. This emphasizes the uniqueness of the cyclopropyl ring as a central platform in stereoselective synthesis.

AB - We report the directed diastereoselective Simmons-Smith cyclopropanation and vanadium-catalyzed epoxidation reactions of alkenyl cyclopropyl carbinol derivatives. The reaction furnished densely substituted stereodefined bicyclopropanes and cyclopropyl oxiranes as a single diastereomer in each case. The remarkable selectivity is obtained thanks to the rigidity of the cyclopropyl core, allowing diastereoselective reactions on the alkenyl moiety. This emphasizes the uniqueness of the cyclopropyl ring as a central platform in stereoselective synthesis.

UR - http://www.scopus.com/inward/record.url?scp=85141987185&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.2c03305

DO - 10.1021/acs.orglett.2c03305

M3 - مقالة

C2 - 36354275

SN - 1523-7060

VL - 24

SP - 8322

EP - 8325

JO - Organic Letters

JF - Organic Letters

IS - 45

ER -

Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this