Hotspot


Organic Letters | 2014

Tertiary Thiols from Allylic Thiocarbamates by Tandem Enantioselective [3,3]-Sigmatropic Rearrangement and Stereospecific Arylation

Gaëlle Mingat; Paul MacLellan; Marju Laars; Jonathan Clayden

The synthesis of tertiary thiols in enantiomerically enriched form is accomplished by lithiation of enantiomerically enriched N-aryl allylic thiocarbamates. Formation of an allyllithium derivative promotes intramolecular N to C aryl migration to the position α to sulfur, generally with good stereospecificity. The substrates may themselves be obtained by Pd-catalyzed enantioselective [3,3]-sigmatropic rearrangement of N-aryl O-allyl thiocarbamates. Solvolysis of the product thiocarbamates yields tertiary thiols, which may be converted to sulfide derivatives.


Acta Crystallographica Section E-structure Reports Online | 2011

rac-2,2′-Bipiperidine-1,1′-diium dibromide

Marju Laars; Kerti Ausmees; Marina Kudrjashova; Tõnis Kanger; Franz Werner

In the title compound, C10H22N2 2+·2Br−, a precursor in the synthesis of organocatalysts, the bipiperidinium ion is located on a twofold rotation axis which passes through the mid-point of the central C—C bond. The piperidinium ring adopts a chair conformation. In the crystal, the cations are linked together by Br− ions through N—H⋯Br hydrogen bonds, forming layers parallel to the ab plane.


Organic Letters | 2006

3,3'-Bimorpholine derivatives as a new class of organocatalysts for asymmetric michael addition

Sarah Sulzer Mosse; Marju Laars; Kadri Kriis; Tõnis Kanger; Alexandre Alexakis


Journal of Organic Chemistry | 2009

Enantioselective Organocatalytic Michael Addition of Aldehydes to β-Nitrostyrenes

Marju Laars; Kerti Ausmees; Merle Uudsemaa; Toomas Tamm; Tõnis Kanger; Margus Lopp


Journal of Organic Chemistry | 2007

Bimorpholine-Mediated Enantioselective Intramolecular and Intermolecular Aldol Condensation

Tõnis Kanger; Kadri Kriis; Marju Laars; Tiiu Kailas; Aleksander-Mati Müürisepp; Tõnis Pehk; Margus Lopp


Tetrahedron-asymmetry | 2008

Structural constraints for C2-symmetric heterocyclic organocatalysts in asymmetric aldol reactions

Marju Laars; Kadri Kriis; Tiiu Kailas; Aleksander-Mati Müürisepp; Tõnis Pehk; Tõnis Kanger; Margus Lopp


Tetrahedron-asymmetry | 2010

Cyclic amino acid salts as catalysts for the asymmetric Michael reaction

Marju Laars; Henri Raska; Margus Lopp; Tõnis Kanger


Chemical Physics Letters | 2009

Influence of protonation upon the conformations of bipiperidine, bimorpholine, and their derivatives

Merle Uudsemaa; Marju Laars; Kadri Kriis; Toomas Tamm; Margus Lopp; Tõnis Kanger


Synthesis | 2007

Synthesis and use of 3,3'-bimorpholine derivatives in asymmetric Michael addition and intramolecular aldol reaction

Sarah Sulzer-Mossé; Marju Laars; Kadri Kriis; Tõnis Kanger; Alexandre Alexakis


Synthesis | 2006

Anchimeric assistance in the case of vicinal dimesylate : Formation of enantiomeric or meso-bimorpholine

Tõnis Kanger; Marju Laars; Kadri Kriis; Tiiu Kailas; Aleksander-Mati Müürisepp; Tõnis Pehk; Margus Lopp

Researchain Logo
Decentralizing Knowledge