133319-25-2

Upstream product

• 4784-77-4 (E)-1-Bromo-2-butene 
• 6057-79-0 (S)-(-)-t-butyl(phenyl)phosphine oxide 
• 133201-85-1 4-((S)-tert-Butyl-phenyl-phosphinoyl)-butan-2-ol 
• 6002-45-5 (+/-)-tert-butyl(phenyl)phosphinothioic O-acid 
• 54100-47-9 (R_p)-(+)-tert-Butylphenylphosphinothioic acid 
• 38802-08-3 (S)-(-)-tert-butylmethylphenylphosphine oxide 
• 644-97-3 Dichlorophenylphosphine 
• 98976-30-8 tert-Butylphenylphosphine oxide 

Downstream Products

• 133201-84-0 (+)-3-<3'-<(S)-tert-butylphenylphosphinoyl>-1'-methylprop-2'-enyl>-2-methyl-2-(3''-oxobut-1''-enyl)cyclopentan-1-one 
• 133201-87-3 (2R,3R)-3-[(R)-3-((S)-tert-Butyl-phenyl-phosphinoyl)-1-methyl-propyl]-2-methyl-2-(3-oxo-butyl)-cyclopentanone 
• 133201-88-4 (1R,7aR)-1-[(R)-3-((S)-tert-Butyl-phenyl-phosphinoyl)-1-methyl-propyl]-7a-methyl-1,2,3,6,7,7a-hexahydro-inden-5-one 
• 133253-02-8 (2R,3R)-3-[(E)-(S)-3-((S)-tert-Butyl-phenyl-phosphinoyl)-1-methyl-allyl]-2-methyl-2-(3-oxo-butyl)-cyclopentanone 
• 133201-89-5 (1R,7aR)-1-[(E)-(S)-3-((S)-tert-Butyl-phenyl-phosphinoyl)-1-methyl-allyl]-7a-methyl-1,2,3,6,7,7a-hexahydro-inden-5-one 

Relevant academic research and scientific papers

Preparation of Enantiomerically Pure Tertiary Phosphine Oxides from, and Assay of Enantiomeric Purity with, (Rp)- and (Sp)-tert-Butylphenylphosphinothioic Acids

A convenient multigram scale method has been developed for preparation of enantiomerically-pure (Rp)- and (Sp)-tertiary phosphine oxides including allyl- and but-2-enyl-tert-butylphenylphosphine oxides wherein (Rp)- and (S

Reaction of metallated tert-butyl(phenyl)phosphane oxide with electrophiles as a route to functionalized tertiary phosphane oxides: Alkylation reactions

P-Chiral tertiary phosphane oxides have been prepared from each of the secondary phosphane oxides racemic 1, (S(p))-(-)-4 and (Rp)-(+)-tert-butylphenylphosphane oxide (5) by lithiation with LDA or nBuLi, or sodiation with sodium hydride, in THF, and then by treatment with a series of primary alkyl halides. Doubly P-chiral ditertiary bis(phosphane oxides) are also obtained from these metallated secondary phosphane oxides by treatment with electrophiles based on straight-chain, tartrate-derived, and bishalomethylarene dihalides. In general, the bis-phosphane oxides are obtained in good yields. However, when the α,ω-dihalide bears an embedded heteroatom (O or Si), yields are diminished. The enantiomeric purity of each of the products was assessed through admixture with (R(p))- and (S(p))-tert-butyl(phenyl)phosphanylthioic acids and measurement of the tert-butyl resonances in the 1H-NMR spectra. In all cases, the act of metallation of the enantiomerically pure secondary phosphane oxide followed by its alkylation is not accompanied by detectable racemization. This method for preparing P-chiral tertiary phosphane oxides is therefore more straightforward than those described previously.

The Preparation of (R)- and (S)-(E)-But-2-enyl-t-butylphenylphosphine Oxides and their Enantiospecific Conversion into Enantiomeric Hydrindenones related to Vitamin D

The individual enantiomers of (E)-but-2-enyl-t-butylphenylphosphine oxide have been prepared, and the lithiated carbanions of each undergo completely stereoselective conjugate addition with 2-methylcyclopent-2-enone to generate enolates, which upon reacti