475301-87-2

Upstream product

• 1461-22-9 tributyltin chloride 
• 218601-55-9 3-phenylpropyl N,N-diisopropylcarbamate 

Downstream Products

• 350589-34-3 Diisopropyl-carbamic acid (R)-1-(1-hydroxy-cyclohex-2-enyl)-3-phenyl-propyl ester 
• 60340-28-5 (S)-1-phenyl-5-hexen-3-ol 
• 60340-28-5 (R)-1-phenyl-hex-5-en-3-ol 
• 1237525-07-3 (5S,6R,7Z)-10-phenyl-6-(trimethylsilyl)dec-7-en-5-ol 
• 1237525-02-8 (1S,2R,3Z)-1,6-diphenyl-2-(trimethylsilyl)hex-3-en-1-ol 
• 1237525-08-4 (1S,2R,3Z)-1-cyclohexyl-6-phenyl-2-(trimethylsilyl)hex-3-en-1-ol 
• 1272031-60-3 N-benzyl-1-(4-methoxyphenyl)-3-phenylpropan-1-amine 
• 1272031-57-8 2-[1-(4-methoxyphenyl)-3-phenylpropyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1449471-86-6 (5S)-3-((2R)-2-((tert-butyldimethylsilyl)oxy)-8-hydroxy-10-phenyldecyl)-5-methyl-3-(phenylthio)dihydrofuran-2(3H)-one 
• 1449471-96-8 (5S)-3-((2R)-2-(tert-butyldimethylsilyloxy)-8-hydroxy-10-phenyldecyl)-3-(4-methoxyphenylthio)-5-methyldihydrofuran-2(3H)-one 
• 1352127-75-3 4,4,5,5-tetramethyl-2-(1-phenylpentan-3-yl)-1,3,2-dioxaborolane 
• 66960-81-4 (S)-3-phenyl-α-d-propanol 
• 601522-90-1 Allyl-((S)-1-phenethyl-but-3-enyl)-amine 
• 350589-41-2 C₁₆H₂₄⁽²⁾HNO₂ 

Relevant academic research and scientific papers

5-substituted derivatives of the tricyclic (+)-sparteine surrogate in the enantioselective lithiation/stannylation of an O-alkyl carbamate

5-Mono- and 5,5-disubstituted tricyclic bispidines, derivatives of the known (+)-sparteine surrogate, have been synthesized in four-to-six steps from the natural alkaloid (-)-cytisine and evaluated as chiral ligands in the enantioselective lithiation/stannylation of an O-alkyl carbamate. Structure-selectivity studies revealed that a small 5-endo substituent is tolerated, whereas larger 5-endo substituents and even small 5-exo substituents lead to significantly reduced levels of chirality transfer. Novel tricyclic bispidines have been synthesized from the readily available alkaloid (-)-cytisine and evaluated in the enantioselective lithiation/stannylation of an O-alkyl carbamate. Structure-selectivity studies revealed that an increased steric demand at the 5-endo position is not favorable.

Catalytic asymmetric deprotonation using a ligand exchange approach

A novel ligand exchange approach to catalytic asymmetric deprotonation-electrophilic trapping has been developed that uses 1.3 equiv of s-BuLi, 0.06-0.2 equiv of chiral diamine ((-)-sparteine or a (+)-sparteine surrogate), and 1.2 equiv of achiral bispidine. The methodology is illustrated with a range of examples and gives access to either enantiomer of useful chiral products in good yields using substoichiometric amounts of chiral diamines. Copyright

A readily-accessible (+)-sparteine surrogate

A "(+)-sparteine-like" chiral diamine, readily synthesized in three steps from (-)-cytisine, has been evaluated in four different asymmetric transformations; in each case, selectivity in an enantiocomplementary fashion to (-)-sparteine was observed. Copyright

On the steric course of transmetallations on enantiomerically defined α-carbamoyloxy organolithiums

The steric courses of the transmetallations of the title organolithiums to the Sn(IV)-, Mg(II)-, Ce(III)-, Zn(II)-, and Cu(I)-species are described.