221467-43-2

Upstream product

• 85-44-9 phthalic anhydride 
• 111061-09-7 (2S,3S)-2-amino-1-phenyl-5-hexen-3-ol 
• 221467-39-6 (2S,3R)-3-(dimethylphenylsilyl)-1-phenyl-2-phthalimido-5-hexen-3-ol 
• 7393-43-3 tetraallyl tin 
• 55722-86-6 (2S)-1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropanal 
• 90365-18-7 N-(p-toluenesulfonyl)-L-phenylalanyl chloride 
• 221467-50-1 (S)-dimethyl(phenyl)(3-phenyl-2-tosylamidopropanoyl)silane 
• 221468-59-3 (2S,3S)-3--4-phenyl-2-tosylamido-5-hexen-3-ol 

Relevant academic research and scientific papers

Tetraallylstannane and Weinreb amides: A simple 'green' route to N-protected homoallylic alcohols and allyl ketones

We have explored the addition of tetraallylstannane (7) to a variety of N-protected Weinreb amides (N-phthalimido and N-benzyl). Reactions were conducted in methanol and the ionic liquid, butylmethylimidazole tetrafluoroborate (bmim[BF4]), yields of the corresponding N-protected allylketones were moderate to good. Allylation of the corresponding aminoaldehydes gave excellent yields of homoallylic alcohols (68-94%) and moderate to good diastereoselectivities (50-86%). (C) 2000 Published by Elsevier Science Ltd.

Synthesis of enantiopure β- and γ-amino alcohols from homochiral α- and β-aminoacylsilanes as stable synthetic equivalents of α- and β-amino aldehydes

A practical route is described for the synthesis of enantiopure β- and γ-amino alcohols with two stereocenters, starting from homochiral α- (1 and 5) and β- (13 and 16) -aminoacylsilanes, and involving stereoselective addition of allylmetal compounds and subsequent stereospecific protiodesilylation of the adducts. The degree of diastereoselectivity achieved in the nucleophilic addition step depends on both the nitrogen- protecting group and the reagents used. Diastereomeric excess (de) values equal to or higher than 98% were obtained in the TiCl4-promoted allylation of the N-Pht aminoacylsilanes 1 and 13 and of the N-Ts-aminoacylsilane 5 with allyltrimethylsilane. Lower de values were obtained in the Sc(OTf)3- catalyzed anylation of 5 with tetraallyltin and in the additions of both allyltrimethylsilane and tetraallyltin to the N-Ts-β-aminoacylsilane 16. Protiodesilylation of the adducts, leading to the β- and γ-amino alcohols, was accomplished with TBAF, except in the case of the adducts obtained from 5. For these, a preliminary removal of the tosyl group was necessary, which was accomplished with simultaneous desilylation by treatment with Na in liquid ammonia.