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Asymmetric 1,4 addition of Grignard reagents to chiral α,β-unsaturated esters in the presence of Lewis acids

✍ Scribed by Giuliana Cardillo; Luca Gentilucci; Alessandra Tolomelli; Claudia Tomasini

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
720 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

The synthesis of enantiomerically enriched a-amino acids is described, by means of the diastereoselective conjugate addition of Grignard reagent to (S)-2-acetamidoacrylic ethoxycarbonylphenyl-methyl ester 1 and its N-Boo derivative 5 in the presence of Lewis acids. The addition of magnesium organocuprates has also been analysed. The reaction proceeds with good yields and variable diastereoselectivities, depending on the organometallic reagent and on the Lewis acid utilised.

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ChemInform Abstract: Asymmetric 1,4 Addi
ChemInform Abstract: Asymmetric 1,4 Addition of Grignard Reagents to Chiral α,β-Unsaturated Esters in the Presence of Lewis Acids.
✍ Giuliana Cardillo; Luca Gentilucci; Alessandra Tolomelli; Claudia Tomasini 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 32 KB 👁 1 views

Asymmetric 1,4 Addition of Grignard Reagents to Chiral α,β-Unsaturated Esters in the Presence of Lewis Acids. -The reaction proceeds with good yields but variable diastereoselectivities, depending on the organometallic reagent and Lewis acid used. -(CARDILLO, GIULIANA;

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Absfruct The 1.4~addition reaction of allyltrimethylsilane to a$-unsaturated N-acyloxa.zolidinones or N-enoyl-soltams ia the presence of Lcwfs acid proceeds in good chemical yield with high d&tereometic excess. The absolute configuration of the new asymmtic center is controlled by the nature of the