Conjugate Additions to Phenylglycinol-Derived Unsaturated δ-Lactams. Enantioselective Synthesis of Uleine Alkaloids

Mercedes Amat; Maria Pérez; Núria Llor; Carmen Escolano; F. Javier Luque; Elies Molins; Joan Bosch

doi:10.1021/jo0487101

Conjugate Additions to Phenylglycinol-Derived Unsaturated δ-Lactams. Enantioselective Synthesis of Uleine Alkaloids

The Journal of Organic Chemistry ◽

10.1021/jo0487101 ◽

2004 ◽

Vol 69 (25) ◽

pp. 8681-8693 ◽

Cited By ~ 38

Author(s):

Mercedes Amat ◽

Maria Pérez ◽

Núria Llor ◽

Carmen Escolano ◽

F. Javier Luque ◽

...

Keyword(s):

Enantioselective Synthesis ◽

Conjugate Additions

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Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers through Copper-Catalyzed Conjugate Additions of Aryl- and Alkylaluminum Reagents to Acyclic Trisubstituted Enones

Angewandte Chemie International Edition ◽

10.1002/anie.201304035 ◽

2013 ◽

Vol 52 (31) ◽

pp. 8156-8159 ◽

Cited By ~ 46

Author(s):

Jennifer A. Dabrowski ◽

Matthew T. Villaume ◽

Amir H. Hoveyda

Keyword(s):

Enantioselective Synthesis ◽

Quaternary Carbon ◽

Conjugate Additions ◽

Stereogenic Centers

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Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers by Catalytic Asymmetric Conjugate Additions of Alkyl and Aryl Aluminum Reagents to Five-, Six-, and Seven-Membered-Ring β-Substituted Cyclic Enones

Angewandte Chemie International Edition ◽

10.1002/anie.200802910 ◽

2008 ◽

Vol 47 (38) ◽

pp. 7358-7362 ◽

Cited By ~ 151

Author(s):

Tricia L. May ◽

M. Kevin Brown ◽

Amir H. Hoveyda

Keyword(s):

Membered Ring ◽

Enantioselective Synthesis ◽

Conjugate Additions ◽

Stereogenic Centers ◽

Cyclic Enones ◽

Catalytic Asymmetric ◽

Quaternary Stereogenic Centers

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ChemInform Abstract: Stereoselective and Enantioselective Synthesis of Five-Membered Rings via Conjugate Additions of Allylsulfone Carbanions

ChemInform ◽

10.1002/chin.200126257 ◽

2010 ◽

Vol 32 (26) ◽

pp. no-no

Author(s):

Alfred Hassner ◽

Eugene Ghera ◽

Tamar Yechezkel ◽

Victoria Kleiman ◽

Thiagarajan Balasubramanian ◽

...

Keyword(s):

Enantioselective Synthesis ◽

Conjugate Additions

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Enantioselective Synthesis of Nitroalkanes Bearing All-Carbon Quaternary Stereogenic Centers through Cu-Catalyzed Asymmetric Conjugate Additions

Journal of the American Chemical Society ◽

10.1021/ja050800f ◽

2005 ◽

Vol 127 (13) ◽

pp. 4584-4585 ◽

Cited By ~ 123

Author(s):

Jing Wu ◽

Dawn M. Mampreian ◽

Amir H. Hoveyda

Keyword(s):

Enantioselective Synthesis ◽

Conjugate Additions ◽

Stereogenic Centers ◽

Quaternary Stereogenic Centers

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Enantioselective Synthesis of Boron-Substituted Quaternary Carbon Stereogenic Centers through NHC-Catalyzed Conjugate Additions of (Pinacolato)boron Units to Enones

Angewandte Chemie International Edition ◽

10.1002/anie.201309982 ◽

2014 ◽

Vol 53 (13) ◽

pp. 3387-3391 ◽

Cited By ~ 75

Author(s):

Suttipol Radomkit ◽

Amir H. Hoveyda

Keyword(s):

Enantioselective Synthesis ◽

Quaternary Carbon ◽

Conjugate Additions ◽

Stereogenic Centers

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Chiral Lewis Acid Catalysis in Conjugate Additions ofO-Benzylhydroxylamine to Unsaturated Amides. Enantioselective Synthesis of β-Amino Acid Precursors

Journal of the American Chemical Society ◽

10.1021/ja980520i ◽

1998 ◽

Vol 120 (26) ◽

pp. 6615-6616 ◽

Cited By ~ 137

Author(s):

Mukund P. Sibi ◽

John J. Shay ◽

Mei Liu ◽

Craig P. Jasperse

Keyword(s):

Amino Acid ◽

Lewis Acid ◽

Acid Catalysis ◽

Enantioselective Synthesis ◽

Lewis Acid Catalysis ◽

Conjugate Additions ◽

Chiral Lewis Acid ◽

Amino Acid Precursors

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Enantioselective Synthesis of Nitroalkanes Bearing All-Carbon Quaternary Stereogenic Centers Through Cu-Catalyzed Asymmetric Conjugate Additions.

ChemInform ◽

10.1002/chin.200533035 ◽

2005 ◽

Vol 36 (33) ◽

Author(s):

Jing Wu ◽

Dawn M. Mampreian ◽

Amir H. Hoveyda

Keyword(s):

Enantioselective Synthesis ◽

Conjugate Additions ◽

Stereogenic Centers ◽

Quaternary Stereogenic Centers

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Highly Diastereoselective and Enantioselective Carbon−Carbon Bond Formations in Conjugate Additions of LithiatedN-Boc Allylamines to Nitroalkenes: Enantioselective Synthesis of 3,4- and 3,4,5-Substituted Piperidines Including (−)-Paroxetine

Journal of the American Chemical Society ◽

10.1021/ja005748w ◽

2001 ◽

Vol 123 (5) ◽

pp. 1004-1005 ◽

Cited By ~ 83

Author(s):

Timothy A. Johnson ◽

Michael D. Curtis ◽

Peter Beak

Keyword(s):

Enantioselective Synthesis ◽

Conjugate Additions ◽

Carbon Bond ◽

Carbon Carbon Bond

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Enantioselective synthesis of peperomins A, C, D, and analogs Examination of diastereoselective cuprate conjugate additions to N-enoyl-4-diphenylmethyl-2-oxazolidinones

Canadian Journal of Chemistry ◽

10.1139/v01-130 ◽

2001 ◽

Vol 79 (11) ◽

pp. 1546-1555 ◽

Cited By ~ 2

Author(s):

Mukund P Sibi ◽

Michael D Johnson ◽

T Punniyamurthy

Keyword(s):

Total Synthesis ◽

Conjugate Addition ◽

Enantioselective Synthesis ◽

Conjugate Additions

A concise and general route to secolignans has been developed. The first total synthesis of secolignans peperomin A (1a), peperomin C (1b), and peperomin D (1c) was accomplished in ~28% overall yield over five synthetic steps. Peperomin analogs (1d) and (1e), possessing two differentially substituted aryl groups, were synthesized by a highly selective conjugate addition. The overall yield for the analogs 1d and 1e were 27 and 26%, respectively.Key words: peperomins, secoliganans, conjugate additions, 4-diphenylmethyl-oxazolidin-2-one.

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ChemInform Abstract: Enantioselective Synthesis of Peperomins A, C, D, and Analogues - Examination of Diastereoselective Cuprate Conjugate Additions to N-Enoyl-4-diphenylmethyl-2-oxazolidinones.

ChemInform ◽

10.1002/chin.200226221 ◽

2010 ◽

Vol 33 (26) ◽

pp. no-no

Author(s):

Mukund P. Sibi ◽

Michael D. Johnson ◽

T. Punniyamurthy

Keyword(s):

Enantioselective Synthesis ◽

Conjugate Additions

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Conjugate Additions to Phenylglycinol-Derived Unsaturated δ-Lactams. Enantioselective Synthesis of Uleine Alkaloids

Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers through Copper-Catalyzed Conjugate Additions of Aryl- and Alkylaluminum Reagents to Acyclic Trisubstituted Enones

Enantioselective Synthesis of All-Carbon Quaternary Stereogenic Centers by Catalytic Asymmetric Conjugate Additions of Alkyl and Aryl Aluminum Reagents to Five-, Six-, and Seven-Membered-Ring β-Substituted Cyclic Enones

ChemInform Abstract: Stereoselective and Enantioselective Synthesis of Five-Membered Rings via Conjugate Additions of Allylsulfone Carbanions

Enantioselective Synthesis of Nitroalkanes Bearing All-Carbon Quaternary Stereogenic Centers through Cu-Catalyzed Asymmetric Conjugate Additions

Enantioselective Synthesis of Boron-Substituted Quaternary Carbon Stereogenic Centers through NHC-Catalyzed Conjugate Additions of (Pinacolato)boron Units to Enones

Chiral Lewis Acid Catalysis in Conjugate Additions ofO-Benzylhydroxylamine to Unsaturated Amides. Enantioselective Synthesis of β-Amino Acid Precursors

Enantioselective Synthesis of Nitroalkanes Bearing All-Carbon Quaternary Stereogenic Centers Through Cu-Catalyzed Asymmetric Conjugate Additions.

Highly Diastereoselective and Enantioselective Carbon−Carbon Bond Formations in Conjugate Additions of LithiatedN-Boc Allylamines to Nitroalkenes: Enantioselective Synthesis of 3,4- and 3,4,5-Substituted Piperidines Including (−)-Paroxetine

Enantioselective synthesis of peperomins A, C, D, and analogs  Examination of diastereoselective cuprate conjugate additions to N-enoyl-4-diphenylmethyl-2-oxazolidinones

ChemInform Abstract: Enantioselective Synthesis of Peperomins A, C, D, and Analogues - Examination of Diastereoselective Cuprate Conjugate Additions to N-Enoyl-4-diphenylmethyl-2-oxazolidinones.

Enantioselective synthesis of peperomins A, C, D, and analogs Examination of diastereoselective cuprate conjugate additions to N-enoyl-4-diphenylmethyl-2-oxazolidinones