Subtilisin integrated artificial plant-cell walls (APCWs) were fabricated by self-assembly using cellulose or nanocellulose as the main component. The resulting APCW catalysts are excellent heterogeneous catalysts for the asymmetric synthesis of (S)-amides. This was demonstrated by the APCW-catalyzed kinetic resolution of several racemic primary amines to give the corresponding (S)-amides in high yields with excellent enantioselectivity. The APCW catalyst can be recycled for multiple reaction cycles without loss of enantioselectivity. The assembled APCW catalyst was also able to cooperate with a homogeneous organoruthenium complex, which allowed for the co-catalytic dynamic kinetic resolution (DKR) of a racemic primary amine to give the corresponding (S)-amide in high yield. The APCW/Ru co-catalysis constitutes the first examples of DKR of chiral primary amines when subtilisin is used as a co-catalyst.

Classical Crabbé type SN 2' substitutions of propargylic substrates has served as one of the standard methods for the synthesis of allenes. However, the stereospecific version of this transformation often requires either stoichiometric amounts of organocopper reagents or special functional groups on the substrates, and the chirality transfer efficiency is also capricious. Herein, we report a sustainable methodology for the synthesis of diverse 1,3-di and tri-substituted allenes by using a simple and cheap cellulose supported heterogeneous nanocopper catalyst (MCC-Amp-Cu(I/II)). This approach represents the first example of heterogeneous catalysis for the synthesis of chiral allenes. High yields and excellent enantiospecificity (up to 97 % yield, 99 % ee) were achieved for a wide range of di- and tri-substituted allenes bearing various functional groups. It is worth noting that the applied heterogeneous catalyst could be recycled at least 5 times without any reduced reactivity. To demonstrate the synthetic utility of the developed protocol, we have applied it to the total synthesis of several chiral allenic natural products.

Efficient reaction conditions are developed for the Pd-catalyzed oxidative carbocyclization-borylation of enallenes to allow the selective formation of cyclobutenes.

Two catalysts consisting of palladium nanoparticles supported either on a siliceous mesocellular foam (PDC-1) or on a metal-organic framework (PDC-2) are evaluated in the title reaction of some unsaturated substrates and compared with the results obtained from Pd-C.

A mild and facile protocol for preparation of allenes is developed.

Allenic alcohols (I) can be readily cyclized to 2-substituted 2,3-dihydrofurans using Shvo′s ruthenium catalyst.

ChemInformVolume 47, Issue 4 Isocyclic Compounds ChemInform Abstract: Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C—H Activation/Carbocyclization of Arylallenes. Javier Mazuela, Javier Mazuela Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorDebasis Banerjee, Debasis Banerjee Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorJan-E. Baeckvall, Jan-E. Baeckvall Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this author Javier Mazuela, Javier Mazuela Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorDebasis Banerjee, Debasis Banerjee Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorJan-E. Baeckvall, Jan-E. Baeckvall Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this author First published: 07 January 2016 https://doi.org/10.1002/chin.201604087Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract This novel and efficient title reaction gives access to synthetically important functionalized indenes. References Javier Mazuela, Debasis Banerjee, Jan-E. Baeckvall, Palladium(II)-Catalyzed Tandem Oxidative Acetoxylation/ortho C.lb.H Activation/Carbocyclization of Arylallenes., J. Am. Chem. Soc., 2015, 137, 9559–9562. DOI: 10.1021/jacs.5b06068; 10.1021/jacs.5b06068 CASPubMedWeb of Science®Google Scholar Volume47, Issue4January, 2016 ReferencesRelatedInformation

The reaction shows good tolerance towards a range of functional groups.

AbstractAn operationally simple protocol for the Pd‐catalyzed oxidative carbocyclization followed by the carbonylative Sonogashira reaction of enallenes is developed to yield functionalized cyclopentenes in good to excellent yields.

AbstractAn oxidative cyclization of allenes in the presence of (Bpin)2 is developed using p‐benzoquinone as the oxidant and Pd(OAc)2 and an axially chiral bisphenol‐type phosphinic acid as catalysts.

A novel protocol for the synthesis of tetrasubstituted olefins through a biomimetic approach has been explored. Both mono- and diarylations were performed under ambient oxygen pressure, giving a range of highly hindered tetrasubstituted alkenes. For diarylation of disubstituted substrates, it was demonstrated that the second arylation is the rate-limiting step of the overall transformation.

AbstractThis new domino reaction of substrates of type (I), (VII), and (X) gives various cyclopentene diester derivatives.

ChemInformVolume 45, Issue 30 Heterocyclic Compounds ChemInform Abstract: Cycloisomerization of Acetylenic Acids to γ-Alkylidene Lactones Using a Palladium(II) Catalyst Supported on Amino-Functionalized Siliceous Mesocellular Foam. Anuja Nagendiran, Anuja Nagendiran Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorOscar Verho, Oscar Verho Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorClemence Haller, Clemence Haller Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorEric V. Johnston, Eric V. Johnston Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorJan-E. Baeckvall, Jan-E. Baeckvall Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this author Anuja Nagendiran, Anuja Nagendiran Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorOscar Verho, Oscar Verho Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorClemence Haller, Clemence Haller Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorEric V. Johnston, Eric V. Johnston Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this authorJan-E. Baeckvall, Jan-E. Baeckvall Dep. Org. Chem., Arrhenius Lab., Univ. Stockholm, S-106 91 Stockholm, Swed.Search for more papers by this author First published: 10 July 2014 https://doi.org/10.1002/chin.201430122Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume45, Issue30July 29, 2014 RelatedInformation

The method offers a useful access to a broad spectrum of acyloxylated vinylallenes.

AbstractDepending on the reaction conditions a selectivity <80% for either the borylated trienes or the borylated vinylallenes is achieved in the product mixtures.

AbstractThe reaction proceeds with complete diastereoselectivity and is scalable.

The key steps of the procedure are dynamic kinetic resolution of alcohols (I) and regio- and stereoselective substitution of the acetates (III).

The reaction is applied to electron‐donating and electron‐withdrawing arylboronic acids tolerating halogens, silyl‐, formyl‐, vinyl‐ and hydroxy‐groups [cf.