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Literature DB >> 15125659

Enantioselective allylation of ketone-derived benzoylhydrazones: practical synthesis of tertiary carbinamines.

Richard Berger¹, Keiko Duff, James L Leighton.

Abstract

A highly practical method for the enantioselective allylation of ketone-derived benzoylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of benzoylhydrazones to give the hydrazide products with good to excellent enantioselectivity (84-97% ee). A mechanism in which the acylhydrazone becomes caovalently attached to the silane has been established.

Entities: Chemical

Year: 2004 PMID： 15125659 DOI： 10.1021/ja0486418

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

11 in total

1. Primary tert- and sec-allylamines via palladium-catalyzed hydroamination and allylic substitution with hydrazine and hydroxylamine derivatives.

Authors: Adam M Johns; Zhijian Liu; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

2. Nonracemic 3 degrees-carbamines from the asymmetric allylboration of N-trimethylsilyl ketimines with B-allyl-10-phenyl-9-borabicyclo[3.3.2]decanes.

Authors: Eda Canales; Eliud Hernandez; John A Soderquist
Journal: J Am Chem Soc Date: 2006-07-12 Impact factor: 15.419

Enantioselective allylation of ketone-derived benzoylhydrazones: practical synthesis of tertiary carbinamines.

1. Primary tert- and sec-allylamines via palladium-catalyzed hydroamination and allylic substitution with hydrazine and hydroxylamine derivatives.

2. Nonracemic 3 degrees-carbamines from the asymmetric allylboration of N-trimethylsilyl ketimines with B-allyl-10-phenyl-9-borabicyclo[3.3.2]decanes.

3. A more comprehensive and highly practical solution to enantioselective aldehyde crotylation.

4. Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling.

5. Highly enantioselective Mannich reactions with α-aryl silyl ketene acetals and imines.

6. Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols.

7. Regiodivergent and Diastereoselective CuH-Catalyzed Allylation of Imines with Terminal Allenes.

8. Enantioselective (formal) aza-Diels-Alder reactions with non-Danishefsky-type dienes.

9. Asymmetric allylboration of acyl imines catalyzed by chiral diols.

10. Asymmetric synthesis of α-allyl-α-aryl α-amino acids by tandem alkylation/π-allylation of α-iminoesters.