5-(Pyrrolidin-2-yl)tetrazole-catalyzed aldol and mannich reactions: acceleration and lower catalyst loading in a continuous-flow reactor.

  title={5-(Pyrrolidin-2-yl)tetrazole-catalyzed aldol and mannich reactions: acceleration and lower catalyst loading in a continuous-flow reactor.},
  author={Arjan Odedra and Peter H. Seeberger},
  journal={Angewandte Chemie},
  volume={48 15},
Continuous organocatalysis: Fast aldol and Mannich reactions require less catalyst when conducted in a microreactor. A proline tetrazole derivative (5-10 mol %) catalyzes asymmetric aldol reactions between various aromatic aldehydes and ketones in microreactor at 60 degrees C with reaction times ranging from 10 to 30 min. 
Silica-supported 5-(pyrrolidin-2-yl)tetrazole: development of organocatalytic processes from batch to continuous-flow conditions
5-(Pyrrolidin-2-yl)tetrazole functionalized silica prepared by photoinduced thiol–ene coupling is packed into a short stainless steel column. The resulting packed-bed microreactor is convenientlyExpand
Asymmetric copper-catalyzed fluorination of cyclic β-keto esters in a continuous-flow microreactor.
A highly enantioselective homogeneous fluorination of cyclic β-keto esters catalyzed by diphenylamine linked bis(oxazoline)-Cu(OTf)2 complexes has been established in a continuous flow microreactor.Expand
Mannich-Type Reactions of Aldimines and Hetero Diels-Alder Reactions of Aldehydes Catalyzed by Anion-Type Lewis Bases Derived from a Single Molecule
Mannich-type reactions of aldimines with silyl enolates and hetero Diels-Alder reactions of aldehydes with Danishef-sky’s diene in the presence of anion catalysts derived from proline were performedExpand
Toward the optimization of continuous-flow aldol and α-amination reactions by means of proline-functionalized silicon packed-bed microreactors
The activity and stability under flow conditions of covalently and non-covalently silica supported proline and proline-like organocatalysts is herein described. The slow aldol reaction ofExpand
Asymmetric anti-Mannich reactions in continuous flow
A polystyrene-supported, pyrrolidine-based catalyst depicting very high activity and excellent stereoselectivity in the anti-Mannich reaction of aldehydes and ketones has been developed. The veryExpand
Conversion of Arylboronic Acids to Tetrazoles Catalyzed by ONO Pincer-Type Palladium Complex.
A convenient synthesis of a library of tetrazoles through a novel and operationally simple protocol effecting the direct conversion of arylboronic acids catalyzed by a new ONO pincer-type Pd(II)Expand
The study of Friedel–Crafts alkylation reaction of thiophenes with glyoxylate imine catalyzed by Fe(III): an easy access to α-aminoesters
A FriedeleCrafts alkylation reaction of thiophenes with glyoxylate imine was developed to give a-aminoesters. In the presence of FeCl3$6H2O as the catalyst, various a-aminoesters were prepared withExpand
Synthesis of β-fluoro(dicarbonyl)ethylamines from 2-fluoro-ethylacetoacetate and dimethyl-2-fluoromalonate ester by batch and semi-continuous flow three-component Mannich reactions
Abstract Multi-component Mannich reactions between 2-fluoro-ethylacetoacetate or dimethyl-2-fluoromalonate ester, aldehyde and amine components allowing convenient synthesis ofExpand
Novel aminoimidazole derived proline organocatalysts for aldol reactions
Abstract A series of l -proline amides with 2-aminoimidazole have been synthesized and found to be highly efficient organocatalysts for aldol reactions when an appropriate acid was added to controlExpand
A silver(i)-catalyzed cascade bicyclization strategy for synthesis of 5H-benzo[d]tetrazolo[5,1-b][1,3]thiazines.
A simple and efficient protocol for silver(i)-catalyzed tandem reaction of o-alkynylphenyl isothiocyanates with sodium azide has been developed, affording a series ofExpand


5‐(Pyrrolidine‐2‐yl)tetrazole: Rationale for the Increased Reactivity of the Tetrazole Analogue of Proline in Organocatalyzed Aldol Reactions
5-(Pyrrolidine-2-yl)tetrazole: Rationale for the Increased Reactivity of the Tetrazole Analogue of Proline in Organocatalyzed Aldol Reaction
A Direct Organocatalytic Entry to Selectively Protected Aldopentoses and Derivatives
The proline-catalysed aldol reaction of 2,2-dimethyl-1,3-dioxan-5-one with dimethoxyacetaldehyde is used as the key reaction according to the biomimetic C 3 +Cn strategy for de novo carbohydrateExpand
Catalytic asymmetric synthesis of a nitrogen analogue of dialkyl tartrate by direct mannich reaction under phase-transfer conditions.
[reaction: see text] Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization ofExpand
Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-alder reactions.
The contributions of this laboratory to converting enzymatic enamines, and in some cases imines, into a versatile catalytic asymmetric strategy powered by small organic molecules are summarized. Expand
Highly enantioselective direct syn- and anti-aldol reactions of dihydroxyacetones catalyzed by chiral primary amine catalysts.
We present herein simple primary-tertiary diamine-Brønsted acid conjugates that catalyze both syn- and anti-aldol reactions of dihydroxyacetones (DHAs) with high diastereoselectivities andExpand
Catalytic, asymmetric transannular aldolizations: total synthesis of (+)-hirsutene.
An asymmetric, catalytic transannular aldolization that provides polycyclic products useful for natural product synthesis and has been demonstrated in a total synthesis of (+)-hirustene. Expand
Efficient Entry to Amino Sugars and Derivatives via Asymmetric Organo­catalytic Mannich Reactions
An efficient biomimetic C 3 +C n entry to amino sugars and derivatives via a direct asymmetric organocatalytic Mannich methodology employing 2,2-dimethyl-l,3-dioxan-5-one as a dihydroxyacetoneExpand
Thermal effects in the organocatalytic asymmetric Mannich reaction.
The proline-catalyzed direct asymmetric Mannich reaction between cyclohexanone, formaldehyde, and various anilines is thermally accelerated and in situ reduction of the resulting ketones affords N-aryl amino alcohols in up to 86% yield. Expand
Direct asymmetric organocatalytic de novo synthesis of carbohydrates
A biomimetic organocatalytic asymmetric synthesis of carbohydrates can be accomplished by a proline catalyzed aldol reaction with the dihydroxyacetone equivalent 2,2-dimethyl-1,3-dioxan-5-one andExpand
Seebach’s oxazolidinone is a good catalyst for aldol reactions
Abstract Seebach’s proline-derived oxazolidinone 2d overcomes (S)-proline and is at least as efficient as (S)-5-(pyrrolidin-2-yl)tetrazole in several organocatalytic aldol reactions examined. A quickExpand