Radical-Polar Crossover Annulation: A Platform for Accessing Polycyclic Cyclopropanes

被引：21

作者：

Milligan, John A. ^{[1
]}

Burns, Kevin L. ^{[2
,3
]}

Le, Anthony, V ^{[2
,3
]}

Polites, Viktor C. ^{[1
]}

Wang, Zheng-Jun ^{[1
,4
]}

Molander, Gary A. ^{[1
]}

Kelly, Christopher B. ^{[2
,3
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, 231 South 34th St, Philadelphia, PA 19104 USA

[2] Virginia Commonwealth Univ, Dept Chem, 1001 West Main St,POB 842006, Richmond, VA 23284 USA

[3] Virginia Commonwealth Univ, Med All Inst, Biotech 8,737 North Fifth St, Richmond, VA 23219 USA

[4] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 41000, Hunan, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 01期

关键词：

Cyclopropanes; Photoredox Catalysis; Cyclization; Radical; Polar Crossover; Radicals; CATALYZED CYCLOPROPANATION; CONSTRUCTION; GENERATION; ALKYLATION; DISCOVERY; ALKENES; ENABLES; POTENT;

D O I：

10.1002/adsc.201901051

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Photoredox-mediated radical/polar crossover (RPC) processes provide unique solutions to challenging annulations. Herein, we describe an approach to the cyclopropanation of olefins that are embedded within bicyclic scaffolds. Whereas these systems are notoriously recalcitrant toward classical cyclopropanation approaches, RPC cyclopropanation can be executed with ease, leading to polycarbocyclic and polyheterocyclic cyclopropanes. The cyclopropanation proceeds through a photoredox-enabled Giese-type radical addition followed by an intramolecular anionic substitution reaction on a neopentyl leaving group.

引用

页码：242 / 247

页数：6

共 36 条

[1] Non-stabilized diazoalkane synthesis via the oxidation of free hydrazones by iodosylbenzene and application in in situ MIRC cyclopropanation [J].

Allouche, Emmanuelle M. D. ;

Charette, Andre B. .

CHEMICAL SCIENCE, 2019, 10 (13) :3802-3806

[2] Iron-catalyzed synthesis of cyclopropanes by in situ generation and decomposition of electronically diversified diazo compounds [J].

Allouche, Emmanuelle M. D. ;

Al-Saleh, Afnan ;

Charette, Andre B. .

CHEMICAL COMMUNICATIONS, 2018, 54 (94) :13256-13259

[3] Scope and Limitations of Cyclopropanations with Sulfur Ylides [J].

Appel, Roland ;

Hartmann, Nicolai ;

Mayr, Herbert .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (50) :17894-17900

[4] Visible Light Photocatalysis for the Generation and Use of Reactive Azolyl and Polyfluoroaryl Intermediates [J].

Arora, Amandeep ;

Weaver, Jimmie D. .

ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2273-2283

[5] Asymmetric Cyclopropanation Reactions [J].

Bartoli, Giuseppe ;

Bencivenni, Giorgio ;

Dalpozzo, Renato .

SYNTHESIS-STUTTGART, 2014, 46 (08) :979-1029

[6] Preparation of conformationally constrained α2 antagonists:: The bicyclo[3.1.0]hexane approach [J].

Bonnaud, B ;

Funes, P ;

Jubault, N ;

Vacher, B .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (15) :3360-3369

[7] Carbonylation of Alkyl Radicals Derived from Organosilicates through Visible-Light Photoredox Catalysis [J].

Cartier, Alex ;

Levernier, Etienne ;

Corce, Vincent ;

Fukuyama, Takahide ;

Dhimane, Anne-Lise ;

Ollivier, Cyril ;

Ryu, Ilhyong ;

Fensterbank, Louis .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (06) :1789-1793

[8]

Charette A.B., 2001, ORG REACT, V58, P1, DOI DOI 10.1002/0471264180.OR058.01

[9] INTRAMOLECULAR REACTIONS OF OLEFINIC DIAZO KETONES [J].

FAWZI, MM ;

GUTSCHE, CD .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (05) :1390-&

[10] PENTACOORDINATE SILICON DERIVATIVES .2. SALTS OF BIS(OMICRON-ARYLENEDIOXY)ORGANOSILICONIC ACIDS [J].

FRYE, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (15) :3170-&

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