Highly enantioenriched 2-azabenzonorbornenes from 7-azabenzonorbornadienes by asymmetric hydroboration-oxidation and tandem deoxygenation-rearrangement-electrophile trapping

Highly enantioenriched 2-azabenzonorbornenes from 7-azabenzonorbornadienes by asymmetric hydroboration-oxidation and tandem deoxygenation-rearrangement-electrophile trapping

3-exo-Substituted 2-azabenzonorbornenes are accessible from 7-azabenzonorbornadienes in good yields and high enantiomeric excess via asymmetric hydroboration-oxidation, followed by tandem deoxygenation- rearrangement-electrophile trapping and also provide access to substituted aminomethylindenes. ©...

Fuld beskrivelse

Bibliografiske detaljer
Main Authors:	Hodgson, D, Winning, L
Format:	Journal article
Sprog:	English
Udgivet:	2006

Lignende værker

Radical cascades using enantioenriched 7-azabenzonorbornenes and their applications in synthesis
af: Hodgson, D, et al.
Udgivet: (2008)

Radical cascades using enantioenriched 7-azabenzonorbornenes and their applications in synthesis.
af: Hodgson, D, et al.
Udgivet: (2008)

Radical cascades using enantioenriched 7-azabenzonorbornenes and their applications in synthesis
af: David M. Hodgson, et al.
Udgivet: (2008-10-01)

Nickel/Bis(oxazoline)-Catalyzed Asymmetric Negishi Arylations of Racemic Secondary Benzylic Electrophiles to Generate Enantioenriched 1,1-Diarylalkanes
af: Do, Hien-Quang, et al.
Udgivet: (2018)

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles
af: Péter Kisszékelyi, et al.
Udgivet: (2023-05-01)

Electrophile dependent mechanisms in the asymmetric trapping of α-lithio-N-(tert-butoxythiocarbonyl)azetidine
af: Delany, PK, et al.
Udgivet: (2020)

Deprotonation-electrophile trapping of terminal epoxides.
af: Hodgson, D, et al.
Udgivet: (2005)

Lithiation: Electrophile trapping of simple aziridine building blocks
af: Hughes, S, et al.
Udgivet: (2007)

Substituted aziridines by lithiation-electrophile trapping of terminal aziridines.
af: Hodgson, D, et al.
Udgivet: (2005)

Synthesis of (−)-6,7-dideoxysqualestatin H5 by carbonyl ylide cycloaddition–rearrangement and cross-electrophile coupling
af: Fegheh-Hassanpour, Y, et al.
Udgivet: (2017)

A catalytic asymmetric bioorganic route to enantioenriched tetrahydro- and dihydropyranones.
af: Baker-Glenn, C, et al.
Udgivet: (2005)

Chiral sulfide and achiral sulfonic acid cocatalyzed enantioselective electrophilic tandem selenylation semipinacol rearrangement of allenols
af: Ren-Fei Cao, et al.
Udgivet: (2025-03-01)

Hydroboration of an alkene by amine-boranes catalysed by a [Rh(PR3)2]+ fragment. Mechanistic insight and tandem hydroboration/dehydrogenation.
af: Sewell, L, et al.
Udgivet: (2011)

On the possibility of carbamate-directed hydroboration. An approach to the asymmetric synthesis of 1-aminocyclopentane-1,3-dicarboxylic acid
af: Hodgson, D, et al.
Udgivet: (1999)

Terminal aziridines by alpha-deprotonation/electrophile trapping of N-protected aziridine.
af: Hodgson, D, et al.
Udgivet: (2008)

Enantioenriched a-substituted aldehydes via diastereoselective enamine alkylation
af: Kaka, N, et al.
Udgivet: (2007)

Enantioselective synthesis of epoxides by alpha-deprotonation--electrophile trapping of achiral epoxides.
af: Hodgson, D, et al.
Udgivet: (2003)

Synthesis of enantioenriched sulfoxides
af: Graham E. O’Mahony, et al.
Udgivet: (2011-03-01)

Catalytic asymmetric radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes to versatile enantioenriched-fluoroalkyl amines
af: Jin-Shun Lin, et al.
Udgivet: (2017-03-01)

Synthesis of azabicyclic systems using nitrogen-directed radical rearrangements.
af: Hodgson, D, et al.
Udgivet: (2007)

trans-Hydroboration–oxidation products in Δ5-steroids via a hydroboration-retro-hydroboration mechanism
af: Hilario-Martínez, JC, et al.
Udgivet: (2020)

The hydroboration of enamines
af: Christian T. Goralski, et al.
Udgivet: (2012-07-01)

Asymmetric electrophilic fluorocyclization with carbon nucleophiles.
af: Wolstenhulme, JR, et al.
Udgivet: (2013)

Tandem intermolecular radical addition-rearrangement for azacycle synthesis
af: Hodgson, D, et al.
Udgivet: (2004)

Enantioselective synthesis of tertiary boronic esters through catalytic asymmetric reversed hydroboration
af: Tao-Tao Gao, et al.
Udgivet: (2021-06-01)

ORGN 26-Cyclizations of enantioenriched beta-hydroxyynones: Synthetic route to enantioenriched unsaturated pyranones and furanones
af: Sawicki, M, et al.
Udgivet: (2006)

Asymmetric rearrangement of N-Boc 7-azanorbornene oxide: use of aryllithiums for enantioselective deprotonation
af: Hodgson, D, et al.
Udgivet: (1999)

First direct deprotonation-electrophile trapping of simple epoxides: synthesis of alpha,beta-epoxysilanes from terminal epoxides.
af: Hodgson, D, et al.
Udgivet: (2001)

α-Lithiation-electrophile trapping of N-thiopivaloylazetidin-3-ol: stereoselective synthesis of 2-substituted 3-hydroxyazetidines.
af: Hodgson, D, et al.
Udgivet: (2013)

Generation and electrophile trapping of N-Boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines.
af: Hodgson, D, et al.
Udgivet: (2014)

ORGANOLANTHANIDE-CATALYZED HYDROBORATION OF OLEFINS
af: Harrison, K, et al.
Udgivet: (1992)

ORGANOLANTHANIDE-CATALYZED HYDROBORATION OF OLEFINS
af: Harrison, K, et al.
Udgivet: (1992)

The Crystal Chemistry of Inorganic Hydroborates
af: Radovan Černý, et al.
Udgivet: (2020-09-01)

Organophosphorus-Catalyzed Deoxygenation of Sulfonyl Chlorides: Electrophilic (Fluoroalkyl)sulfenylation by P[superscript III]/Psuperscript V]=O Redox Cycling
af: Ghosh, Avipsa, et al.
Udgivet: (2020)

Lithiation-electrophilic substitution of N-thiopivaloylazetidine.
af: Hodgson, D, et al.
Udgivet: (2010)

A concise synthesis of enantioenriched fluorinated carbocycles.
af: Lam, Y, et al.
Udgivet: (2007)

Cathodic tandem alkylation/dearomatization of heterocycles enabled by Al-facilitated carbonyl deoxygenation
af: Jinhui Hu, et al.
Udgivet: (2025-01-01)

Studies on organolithium-induced alkylative desymmetrisation of epoxides: synthesis of enantioenriched beta-amino cycloheptenols from 6,7-epoxy-8-azabicyclo[3.2.1]octanes
af: Hodgson, D, et al.
Udgivet: (2004)

Ytterbium-catalyzed hydroboration of aldehydes and ketones
af: Wang, Weifan, et al.
Udgivet: (2020)

Synthesis of alpha-kainic acid from a 7-azabicyclo[2.2.1]heptadiene by tandem radical addition-homoallylic radical rearrangement.
af: Hodgson, D, et al.
Udgivet: (2005)