Diastereoselective Cyclopropanation by Using Camphorpyrazolidinone Derived α,β-Unsaturated Amides and Ylide

10.26434/chemrxiv.13298210 ◽

2020 ◽

Author(s):

sudershan gondi

Keyword(s):

Carboxylic Acid ◽

Asymmetric Synthesis ◽

Michael Addition ◽

Chemical Yield ◽

High Chemical ◽

Unsaturated Carboxylic Acid ◽

Optically Pure ◽

The Michael Addition

<p><b>Abstract:</b> High to moderate diastereoselectivity and high chemical yield are observed in the Michael addition of ylide and chiral camphorpyrazolidinone ylide to an optically pure a,b-unsaturated carboxylic acid derivatives derived from a chiral camphorpyrazolidinone and a,b-unsaturated carbonyl respectively. A novel route to the asymmetric synthesis of cyclopropanation derivatives is described.</p>

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Photoredox Michael addition of phenylmalononitrile onto α,β-unsaturated carboxylic acid

Tetrahedron Letters ◽

10.1016/j.tetlet.2020.151824 ◽

2020 ◽

Vol 61 (18) ◽

pp. 151824

Author(s):

Toshiya Hirahama ◽

Misaki Umezawa ◽

Mitsuru Shoji

Keyword(s):

Carboxylic Acid ◽

Michael Addition ◽

Unsaturated Carboxylic Acid

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Optically Pure Aminopolyols and Polyoxamic Acid Derivatives from Aziridine-2-carboxylates

Australian Journal of Chemistry ◽

10.1071/c98026 ◽

1999 ◽

Vol 52 (4) ◽

pp. 259 ◽

Cited By ~ 10

Author(s):

Heribert Dollt ◽

Volker Zabel

Keyword(s):

Solvent Effects ◽

Michael Addition ◽

Building Blocks ◽

Bulky Substituent ◽

Cis And Trans ◽

Optically Pure ◽

The Michael Addition

Various new chiral building blocks could easily be prepared from optically pure cis and trans ethyl 3-(1′,3′- dioxolan-4′-yl)aziridine-2-carboxylates. A stereochemically pure 1,3-dioxolan in the allyl position of an α-bromoacrylate induced a high (3R*,4′S*) selectivity in the Michael addition with an amine. After oxygen at the inducing centre was exchanged with nitrogen bearing a bulky substituent, the directing influence of this new group was examined. Solvent effects influencing the cis/trans ratio of aziridine formation are discussed.

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Asymmetric Synthesis of β-Amino Acids via the Michael Addition of Chiral Metal Amides

Journal of Synthetic Organic Chemistry Japan ◽

10.5059/yukigoseikyokaishi.55.26 ◽

1997 ◽

Vol 55 (1) ◽

pp. 26-34 ◽

Cited By ~ 16

Author(s):

Stephen G. DAVIES ◽

Osamu ICHIHARA

Keyword(s):

Amino Acids ◽

Asymmetric Synthesis ◽

Michael Addition ◽

Metal Amides ◽

The Michael Addition

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Unique reactivity of ?,?-unsaturated carboxylic acid imidazolides: Catalytic asymmetric synthesis of ?,?-epoxy esters and ?,?-epoxy carboxylic acid derivatives

Chirality ◽

10.1002/chir.10205 ◽

2003 ◽

Vol 15 (4) ◽

pp. 306-311 ◽

Cited By ~ 10

Author(s):

Tetsuhiro Nemoto ◽

Shin-Ya Tosaki ◽

Takashi Ohshima ◽

Masakatsu Shibasaki

Keyword(s):

Carboxylic Acid ◽

Asymmetric Synthesis ◽

Unsaturated Carboxylic Acid ◽

Catalytic Asymmetric Synthesis ◽

Catalytic Asymmetric

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Michael Addition of Thioacetic Acid to α, β-Unsaturated Carboxylic Acid Esters in the Presence of Clays or Zeolites

Journal of Japan Oil Chemists Society ◽

10.5650/jos1996.46.899 ◽

1997 ◽

Vol 46 (8) ◽

pp. 899-903,938

Author(s):

Masayuki NISHI ◽

Hisashi FUJIHARA ◽

Masakuni YOSHIHARA ◽

Toshihisa MAESHIMA

Keyword(s):

Carboxylic Acid ◽

Michael Addition ◽

Thioacetic Acid ◽

Unsaturated Carboxylic Acid ◽

Acid Esters

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Organocatalytic Asymmetric Michael Addition of Ketones to α, β-Unsaturated Nitro Compounds

Catalysts ◽

10.3390/catal10060618 ◽

2020 ◽

Vol 10 (6) ◽

pp. 618 ◽

Cited By ~ 1

Author(s):

Jae Ho Shim ◽

Si Hun Nam ◽

Byeong-Seon Kim ◽

Deok-Chan Ha

Keyword(s):

Michael Addition ◽

Chemical Yield ◽

Nitro Compounds ◽

Neutral Condition ◽

High Chemical ◽

Aromatic Ketones ◽

Michael Additions ◽

Asymmetric Michael Addition ◽

Neutral Conditions ◽

Organic Catalyst

An organic catalyst “(R, R)-1,2-diphenylethylenediamine(DPEN) derivative’’ was devel-oped as a chiral bifunctional organocatalyst and applied for asymmetric Michael additions of aromatic ketones to trans-β-nitroalkene compounds under neutral conditions. The isopropyl-subs-tituted thiourea catalyst in neutral condition provides high chemical yield and enantioselectivities (ee) (up to 96% yield, 98% ee).

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