477210-49-4

Upstream product

• 149525-94-0 (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-oxonon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester 
• 113368-89-1 (-)-8-phenylmenthyl dimethyl phosphonoacetate 
• 149525-95-1 (E)-(4R,6R,8S)-6-(benzyloxy)-4,8-bis((tert-butyldiphenylsilyl)oxy)-9-hydroxynon-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester 

Downstream Products

• 477210-51-8 (E)-(4R,6R)-6-Benzyloxy-4-hydroxy-7-(S)-oxiranyl-hept-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 477210-50-7 (E)-(4R,6R,8S)-6-benzyloxy-4,8-dihydroxy-9-(toluene-4-sulfonyloxy)non-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl ester 

Relevant academic research and scientific papers

Asymmetric Horner-Wadsworth-Emmons reactions with Meso-dialdehydes: Scope, mechanism, and synthetic applications

Asymmetric Homer-Wadsworth-Emmons reactions between chiral phosphonate reagents and various meso-dialdehydes have been investigated. A mechanistic model useful for rationalizing the experimentally observed stereoselectivities is presented. Furthermore, st

A versatile stereocontrolled approach to chiral tetrahydrofuran and tetrahydropyran derivatives by use of sequential asymmetric Horner-Wadsworth-Emmons and ring-closure reactions

An approach to chiral tetrahydrofuran and tetrahydropyran derivatives based on the sequential use of an asymmetric Horner-Wadsworth-Emmons reaction and a cyclization step is presented. The approach is both stereochemically and structurally versatile since three different cyclization methods can be employed starting from the same HWE product: (i) palladium-catalyzed substitution, (ii) hetero-Michael addition, or (iii) epoxide opening. The asymmetric HWE reaction controls the absolute configuration of the ultimate product, whereas the relative configuration is controlled by the combined influence of the geometric selectivity in the HWE reaction and the stereochemistry of the respective cyclization method.