61999-35-7

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 65092-79-7 (2R,3S)-3,4-Dimethyl-2-phenyl-6-[1-phenyl-meth-(E)-ylidene]-[1,4]oxazepane-5,7-dione 
• 109-72-8 n-butyllithium 
• 107173-65-9 N-(3-phenylpropenoyl)-L-proline 
• 105526-93-0 (5S)-N-[(3S)-phenylheptanoyl]-5-triphenylmethoxymethyl-2-pyrrolidinone 
• 109-65-9 1-bromo-butane 
• 152529-41-4 (E)-N-(2-Fluoro-benzyl)-N-((R)-1-hydroxymethyl-propyl)-3-phenyl-acrylamide 
• 129287-63-4 (1'S,2R,5R,6R)-2-tert-Butyl-6-methyl-5-(1'-phenylpentyl)-1,3-dioxan-4-on 
• 107289-12-3 (1'RS,2R,5R,6R)-2-(tert-butyl)-5-(α-hydroxybenzyl)-6-methyl-1,3-dioxan-4-one 
• 118356-63-1 (E,2R,6R)-5-Benzyliden-2-tert-butyl-6-methyl-1,3-dioxan-4-on 
• 129287-80-5 (1'R,2R,3S)-2-(1'-Hydroxyethyl)-3-phenylheptansaeure 
• 106189-53-1 N-(3-phenyl-2-propenoyl)-1-ephedrine 
• 152529-40-3 (E)-N-((R)-1-Hydroxymethyl-propyl)-3-phenyl-N-(2,2,2-trifluoro-ethyl)-acrylamide 
• 137623-81-5 (3S)-3-phenylheptan-1-ol 

Relevant academic research and scientific papers

Chiral molecular recognition by aluminum tris(2,6-diphenylphenoxide) in an asymmetric 1,4-addition

A precomplex of a chiral α,β-unsaturated ester and a bulky aluminum oxide is crucial to setting the diastereoselectivity in the 1,4-addition of a Grignard or organolithium reagent. This approach based on chiral recognition broadens the potential of the strategies relying on stoichiometric reagents.

The 1,4-addition of organometallic reagents to enoates derived from pinanediol

The complex-induced, proximity effect-promoted 1,4-addition of RCu·BF3 and R2CuLi to enoates derived from (-)-pinanediol leads to adducts with the opposite sense of chirality (up to 98% d.e.).

Application of (2R,3R)-dihydroxy-1,2,3,4-tetrahydronaphthalene to asymmetric synthesis

(2R,3R)-Dihydroxy-tetrahydronaphthalene, prepared via an efficient chemoenzymatic procedure from naphthalene, has been successfully tested, as a chiral auxiliary in diastereoselective conjugate additions of lithium dialkylcuprates to α,β-unsaturated ester

Diastereoselectivity in Iodotrimethylsilane-promoted Conjugate Additions of Organocopper Reagents to Chiral α,β-Unsaturated Imides and Amides

Conjugate additions of MeCu, PhCu and BuCu to the chiral enoylimides 2 a-c in the presence of iodotrimethylsilane and lithium iodide in THF give the adducts, 4a-c in yields above 90percent and diastereoselectivities from 80 to 93percent.The dominating diastereomers are different from those formed with LiR2Cu/TMSCl or in copper(I)-mediated addition of Grignard reagents.Corresponding additions to enoyl-amides of O-tritylprolinol also give high yields of conjugate adducts, but lower diastereoselectivities, with dominating configuration in the acyl part opposite to those from the imides.

Dispiroketals in synthesis (Part 16): Functionalised dispiroketals as new chiral auxiliaries; the synthesis of dihydroxylated dispiroketals in optically pure form and their application as bifunctional , C2-symmetrical, chiral auxiliaries for highly stereoselective Michael additions

A range of rigid, architecturally complex diols derived from dispiroketals have been synthesised.A bifunctional, C2-symmetrical, chiral auxiliary derived from these dihydroxylated dispiroketals has been used to induce a high degree of asymmetry in Michael additions of cuprates to a variety of di-α,β-unsaturated ester systems.

Enantioselective Michael Additions of Grignard Reagents to Cinnamamides deriving from N-Fluoroalkyl (R)-(-)-2-Aminobutan-1-ol. Determination of Diastereomeric Excess by means of 19F NMR

N-Alkylation of (R)-(-)-2-aminobutan-1-ol 1 (a readily available reagent) with ortho-fluorobenzyl chloride, followed by reaction with cinnamoyl chloride, afforded the cinnamamide (R)-(+)-6.Michael addition of n-alkyl magnesium halides to the latter gave t

(E,R,R)-5-Alkylidene-2-tert-butyl-6-methyl-1,3-dioxan-4-ones: Preparation from (R)-3-Hydroxybutbutyric Acid, Cuprate Additions and Hydrolyses to 3-Hydroxycarboxylic Acids with Chiral Secondary Alkyl Substituents in the 2-Position

Li enolates of (R,R)-2-tert-Butyl-6-methyl-1,3-dioxan-4-one add to aliphatic or aromatic aldehydes with relative topicity Re,Re (2:1 to 10:1, 9 examples).The title compounds are obtained from these aldol adducts by dehydration through mesylates (5 example

Asymmetric Conjugate Addition to Unsaturated Chiral Amido Alcohols Using Grignard Reagents Co-ordinated with Tertiary Amines or DBU. Preparation of Optically Active 3-Substituted Carboxylic Acids and (S)-(-)-Citronellol

Optically active 3-substituted carboxylic acids and (S)-(-)-citronellol have been obtained by diastereoselective conjugate addition of Grignard reagents co-ordinated with 1,8-diazabicyclo-undec-7-ene (DBU) to chiral amidoalcohols derived from (S)-proline.