Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids

Gurupada Hazra; Sanjay Maity; Sudipto Bhowmick; Prasanta Ghorai

doi:10.1039/c6sc04522g

Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids

Chemical Science ◽

10.1039/c6sc04522g ◽

2017 ◽

Vol 8 (4) ◽

pp. 3026-3030 ◽

Cited By ~ 22

Author(s):

Gurupada Hazra ◽

Sanjay Maity ◽

Sudipto Bhowmick ◽

Prasanta Ghorai

Keyword(s):

Michael Reaction ◽

Boronic Acids ◽

Enantioselective Synthesis ◽

Hydroxy Ketones

An enantioselective synthesis of 3-substituted benzoxaboroles has been developed using organocatalysts with good to excellent enantioselectivities (up to 99%). The resulting benzoxaboroles were converted to the chiral β-hydroxy ketones without affecting the enantioselectivity.

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Enantioselective Synthesis of 3,4-Dihydropyran Derivatives via Organocatalytic Michael Reaction of α,β-Unsaturated Enones

The Journal of Organic Chemistry ◽

10.1021/jo3001047 ◽

2012 ◽

Vol 77 (8) ◽

pp. 4136-4142 ◽

Cited By ~ 41

Author(s):

Yangbin Liu ◽

Xiaohua Liu ◽

Min Wang ◽

Peng He ◽

Lili Lin ◽

...

Keyword(s):

Michael Reaction ◽

Enantioselective Synthesis

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Boronic Acids as Versatile Aryl Sources for the Highly Enantioselective Synthesis of Chiral Diarylmethanols on Multigram Scale

Synthesis ◽

10.1055/s-2004-834887 ◽

2004 ◽

Vol 2005 (05) ◽

pp. 840-842 ◽

Cited By ~ 2

Author(s):

Carsten Bolm ◽

Jens Rudolph ◽

Frank Schmidt

Keyword(s):

Boronic Acids ◽

Enantioselective Synthesis

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Catalytic enantioselective synthesis of α-aryl α-hydrazino esters and amides

Chemical Communications ◽

10.1039/d0cc02478c ◽

2020 ◽

Vol 56 (43) ◽

pp. 5823-5826

Author(s):

Marta Velázquez ◽

Saúl Alberca ◽

Javier Iglesias-Sigüenza ◽

Rosario Fernández ◽

José M. Lassaletta ◽

...

Keyword(s):

Building Blocks ◽

Boronic Acids ◽

Enantioselective Synthesis

Asymmetric 1,2-addition of aryl boronic acids to N-carbamoyl (Cbz and Fmoc) protected glyoxylate-derived hydrazones affords α-aryl α-hydrazino esters/amides, key building blocks en route to artificial peptides.

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Ruthenium–Me-BIPAM-catalyzed addition reaction of aryl-boronic acids to benzofuran-2,3-diones for the enantioselective synthesis of 3-aryl-3-hydroxybenzofuran-2-ones

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2015.10.010 ◽

2015 ◽

Vol 26 (24) ◽

pp. 1430-1435 ◽

Cited By ~ 7

Author(s):

Masaaki Yohda ◽

Yasunori Yamamoto

Keyword(s):

Addition Reaction ◽

Boronic Acids ◽

Enantioselective Synthesis

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Amino alcohol catalyzed direct asymmetric aldol reactions: enantioselective synthesis of anti -α-fluoro-β-hydroxy ketones

Tetrahedron Letters ◽

10.1016/j.tetlet.2004.05.107 ◽

2004 ◽

Vol 45 (29) ◽

pp. 5681-5684 ◽

Cited By ~ 75

Author(s):

Guofu Zhong ◽

Junhua Fan ◽

Carlos F. Barbas

Keyword(s):

Amino Alcohol ◽

Enantioselective Synthesis ◽

Aldol Reactions ◽

Asymmetric Aldol ◽

Hydroxy Ketones

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Stereocontrolled Elaboration of Quaternary Carbon Centers through the Asymmetric Michael Reaction Using Chiral Imines: Enantioselective Synthesis of (+)-Aspidospermidine

The Journal of Organic Chemistry ◽

10.1021/jo00088a008 ◽

1994 ◽

Vol 59 (9) ◽

pp. 2292-2303 ◽

Cited By ~ 71

Author(s):

Didier Desmaeele ◽

Jean d'Angelo

Keyword(s):

Michael Reaction ◽

Enantioselective Synthesis ◽

Quaternary Carbon ◽

Carbon Centers ◽

Asymmetric Michael Reaction ◽

Chiral Imines

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A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2013.01.005 ◽

2013 ◽

Vol 24 (4) ◽

pp. 196-201 ◽

Cited By ~ 12

Author(s):

Gullapalli Kumaraswamy ◽

Dasa Rambabu

Keyword(s):

Michael Reaction ◽

Enantioselective Synthesis ◽

Transfer Hydrogenation ◽

Asymmetric Transfer Hydrogenation ◽

Cross Metathesis ◽

Key Steps

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Catalytic Asymmetric Reductive Coupling of Alkynes and Aldehydes: Enantioselective Synthesis of Allylic Alcohols and α-Hydroxy Ketones

Journal of the American Chemical Society ◽

10.1021/ja034366y ◽

2003 ◽

Vol 125 (12) ◽

pp. 3442-3443 ◽

Cited By ~ 184

Author(s):

Karen M. Miller ◽

Wei-Sheng Huang ◽

Timothy F. Jamison

Keyword(s):

Enantioselective Synthesis ◽

Allylic Alcohols ◽

Reductive Coupling ◽

Hydroxy Ketones ◽

Catalytic Asymmetric

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A New Entry to Enantioselective Synthesis of .ALPHA.-Methylene-.BETA.-hydroxy Ketones by the Chalcogeno-Baylis-Hillman Reaction.

Chemical and Pharmaceutical Bulletin ◽

10.1248/cpb.47.956 ◽

1999 ◽

Vol 47 (7) ◽

pp. 956-961 ◽

Cited By ~ 25

Author(s):

Tetsuo IWAMA ◽

Shin-ichiro TSUJIYAMA ◽

Hironori KINOSHITA ◽

Kiyoko KANEMATSU ◽

Yasuo TSURUKAMI ◽

...

Keyword(s):

Enantioselective Synthesis ◽

Hydroxy Ketones ◽

New Entry

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Highly enantioselective synthesis of α-methylene-δ-valerolactones by an asymmetric Michael reaction

Tetrahedron Asymmetry ◽

10.1016/j.tetasy.2006.03.007 ◽

2006 ◽

Vol 17 (6) ◽

pp. 908-915 ◽

Cited By ~ 10

Author(s):

Henryk Krawczyk ◽

Marcin Śliwiński ◽

Jacek Kędzia ◽

Jakub Wojciechowski ◽

Wojciech M. Wolf

Keyword(s):

Michael Reaction ◽

Enantioselective Synthesis ◽

Asymmetric Michael Reaction

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