Borane-Methyl Sulfide Reductive Cyclization of ω-Ester Alkylamides: A Convenient Synthesis of<i>N</i>-Substituted Cyclic Amines

Venuti, Michael C.; Ort, Oswald

doi:10.1055/s-1988-27777

Cited by 16 publications

(7 citation statements)

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“…Similarly, imine 15 was also reduced under these reaction conditions to amine 16 in good yield and enantioselectivity (96 % ee ). Amine 16 could be a potential intermediate for the synthesis of (+)‐crispine A following the reported procedure 19…”

Section: Methodsmentioning

confidence: 99%

Large Hyperconjugation in Strained Systems

Racine

Humbel

2014

Chemistry A European J

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Carbocations can appear as transient species, for instance, in elimination reactions and various rearrangements. Hyperconjugation (or conjugation) can then stabilize the cationic character and form a partial π bond. The effect of the electronic delocalization from strained substituents to a carbocation part was calculated. Very large hyperconjugation was found, sometimes more than 80 kcal mol(-1) , which is much larger than typical conjugation effects (56 kcal mol(-1) for the allyl cation).

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Section: Methodsmentioning

confidence: 99%

Large Hyperconjugation in Strained Systems

Racine

Humbel

2014

Chemistry A European J

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“…Amine 16 could be ap otentiali ntermediate for the synthesis of (+ +)-crispine Af ollowing the reported procedure. [19] Based on previous reports, [9c,20] am echanism for oxorhenium-catalyzed asymmetricr eduction of ketimineu sing hydrosilane is proposed in Scheme 4. The chiral oxorhenium catalysts undergo al igand displacement to form a h 1 -silane Re V adduct (I), which weakenst he SiÀHb ond.…”

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confidence: 99%

Synthesis of Air‐ and Moisture‐Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction

Das

Nallagonda

Dey

et al. 2015

Chemistry A European J

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Air-/moisture-stable, crystalline, and storable chiral salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α-amino esters, γ- and δ-lactams, and isoindolinones have also been carried out using this methodology. Finally, the method has been applied to synthetic targets of pharmaceutical relevance, such as R-(+)-salsolidine and R-(+)-crispine A.

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“…As shown in Scheme , Michael adduct 4l in the presence of borane‐dimethyl sulfide was converted into chiral indoline‐pyrrolidine adduct 6l in 40 % yield with moderate enantioselectivity (70.6 % ee , Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…The structure along with the relative configuration of 4a was confirmed by single-crystal X-ray crystallography (Figure 3). [10] As shown in Scheme 3, [11] Michael adduct 4l in the presence of borane-dimethyl sulfide was converted into chiral indolinepyrrolidine adduct 6l in 40 % yield with moderate enantioselectivity (70.6 % ee, Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

Organocatalytic Enantioselective Michael Addition of 3‐Indolinone‐2‐Carboxylates to Maleimides

et al. 2018

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An organocatalyzed asymmetric conjugate addition of 2‐substituted 3‐indolinones to maleimides has been developed by using a chiral bifunctional squaramide derived from quinidine to promote the reaction. This method provides easy access to 3‐indolinone‐2‐carboxylate‐succinimide adducts in high yields with excellent diastero and entantioselectivities and is a useful approach for the construction of vicinal quaternary‐tertiary chiral centers. In addition, product 4l was successfully converted into a chiral indoline‐pyrrolidine adduct.

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Borane-Methyl Sulfide Reductive Cyclization of ω-Ester Alkylamides: A Convenient Synthesis ofN-Substituted Cyclic Amines

Cited by 16 publications

References 0 publications

Large Hyperconjugation in Strained Systems

Large Hyperconjugation in Strained Systems

Synthesis of Air‐ and Moisture‐Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction

Organocatalytic Enantioselective Michael Addition of 3‐Indolinone‐2‐Carboxylates to Maleimides

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