An Efficient Synthesis ofN-Phosphorylated Azadienes, Primary (E)-Allylamines, and β-Amino-Phosphane Oxides and -Phosphonates from β-Functionalized Oxime Derivatives

Palácios, Francisco; Aparicio, Domitila; Garcı́a, Jesús M.; Rodriguez, Encina

doi:10.1002/(sici)1099-0690(199807)1998:7<1413::aid-ejoc1413>3.0.co;2-e

Cited by 43 publications

(23 citation statements)

References 81 publications

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“…In another study of reductions of a,b-unsaturated N-phosphinoylketimines, Palacios and coworkers studied acyclic systems 30 (Scheme 14). 23 It was found that these imines can be cleanly reduced with sodium borohydride to afford allylic amine derivatives 31 in good yields.…”

Section: Scheme 13mentioning

confidence: 99%

N-Phosphinoylimines: An Emerging Class of Reactive Intermediates for Stereoselective Organic Synthesis

Weinreb¹,

Orr²

2005

Synthesis

114

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N-Phosphinoylimines have recently begun to attract significant attention from synthetic chemists for the preparation of nitrogen-containing molecules. Several methods have been developed for the synthesis, or in situ generation, of these reactive electrophilic species. N-Phosphinoylimines undergo a wide range of reactions, including nucleophilic additions and cycloadditions. These imines are also effective electrophiles in a number of diastereoselective and enantioselective reactions. An advantage of using N-phosphinoylimines is that the reaction products can be easily deprotected under mild acidic conditions, leading to amines. This review outlines the preparation and uses of N-phosphinoylimines with particular emphasis on their applications in stereoselective processes.

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Section: Scheme 13mentioning

confidence: 99%

N-Phosphinoylimines: An Emerging Class of Reactive Intermediates for Stereoselective Organic Synthesis

Weinreb¹,

Orr²

2005

Synthesis

114

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“…The proposed mechanism entails the formation of a phosphorus (III) oxime ester which upon rearrangement involving radical intermediates finally affords the ketimine 20 . This procedure shows a very large substrate applicability and can also be used for the preparation of N ‐phosphinoyl azadienes from enone oximes [23] . A direct method similar to that employed for the preparation of N‐ sulfonylimines 19 reacting ketones with diphenylphosphinamide in the presence of titanium(IV) ethoxide has been occasionally employed for a limited number of substrates [24] .…”

Section: Preparation Of N‐activated Ketiminesmentioning

confidence: 99%

Enantioselective Catalyzed Synthesis of Amino Derivatives Using Electrophilic Open‐Chain N‐Activated Ketimines

2021

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N‐Activated ketimines are characterized by the presence of acyl, sulfonyl, and phosphinoyl groups linked to the nitrogen atom of the azomethine system. These electron‐withdrawing groups enhance the electrophilic character of the imino moiety allowing the addition of even weak nucleophilic reagents. The presence of the oxygen atoms in these activating groups with its coordinating and Lewis or Brønsted properties is of paramount importance in asymmetric catalyzed reactions. This review collects the results that have appeared in the literature during the last two decades on the utilization of open‐chain N‐activated ketimines for the synthesis of optically active α‐disubstituted and α‐trisubstituted amino derivatives including nitrogen‐containing heterocyclic compounds.

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“…The three steps can be conducted in a one-pot procedure. 220 Asymmetric reduction of α-oxoketoxime ethers using reagents prepared in situ from trimethylborate and chiral amino alcohols derived from α-pinene or -proline result in stereoselective syntheses of 1,2-aminoalcohols. The 1,2-aminoalcohols are obtained in 31-94% yields as predominantly the anti-products and with 31-98% ee.…”

Section: Reduction Of Oximesmentioning

confidence: 99%

Imines, enamines and oximes

Adams¹

1997

Contemp. Org. Synth.

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An Efficient Synthesis ofN-Phosphorylated Azadienes, Primary (E)-Allylamines, and β-Amino-Phosphane Oxides and -Phosphonates from β-Functionalized Oxime Derivatives

Cited by 43 publications

References 81 publications

N-Phosphinoylimines: An Emerging Class of Reactive Intermediates for Stereoselective Organic Synthesis

N-Phosphinoylimines: An Emerging Class of Reactive Intermediates for Stereoselective Organic Synthesis

Enantioselective Catalyzed Synthesis of Amino Derivatives Using Electrophilic Open‐Chain N‐Activated Ketimines

Imines, enamines and oximes

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