59614-86-7

Upstream product

• 100807-68-9 ((S)-1-methyl-heptyl)-malonic acid 
• 917-54-4 methyllithium 
• 3761-92-0 n-hexylmagnesium bromide 
• 116262-07-8 (S)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-methyl-nonan-1-one 
• 111-25-1 1-bromo-hexane 
• 199006-79-6 (R)-(+)-N-(1-ethyl-2-hydroxy)ethyl-N-(2-fluorobenzyl) crotonamide 
• 198956-40-0 (2S)-2-Benzyloctane 
• 49826-80-4 4-(2,2-dimethyl-3-phenylpropyl)-1-fluorobenzene 
• 77727-23-2 (E)-2-((S)-Benzenesulfinyl)-non-2-enoic acid methyl ester 
• 102180-66-5 ((S)1-methyl-heptyl)-malonic acid dibutyl ester 
• 5978-55-2 (2R)-2-bromooctane 
• 104651-12-9 (E)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-methyl-non-2-en-1-one 
• 66967-39-3 [(S)-((E)-Oct-1-ene)-1-sulfinyl]-benzene 
• 21369-64-2 n-hexyllithium 

Downstream Products

• 86414-46-2 (S)-1-bromo-3-methylnonane 

Relevant academic research and scientific papers

Enantioselective carbometalation of cinnamyl derivatives: New access to chiral disubstituted cyclopropanes - Configurational stability of benzylic organozinc halides

A stoichiometric or catalytic amount of (-)-sparteine can serve asa promoter for the enantioselective carbolithiation of cinnamyl derivatives by primary and secondary organolithium compounds. The enantiofacial choice of the addition reaction is dependent on the stereochemistry of the initial double bond. The resulting benzylic organolithium compounds can be derivatized to a linear phenylated chain that bears two contiguous stereogenic centers with given configurations. The use of the dimethyl acetal of the (E)-cinnamyl alcohol allows the highest enantioselective carbolithiation and by simply warming the reaction mixture to room temperature, the resulting benzylic organo-lithium intermediate undergoes a 1,3-elimination to give the chiral disubstituted cyclopropane in high enantiomeric excess (90-95% ee). Another significant finding is the observation that the Li-Zn transmetalation in a benzylic species occurs with inversion of configuration, and the corresponding acyclic benzylic zinc halides have observable configurational stability at - 30°C.

Enantioselective carbolithiation of β-alkylated styrene

Stoichiometric or catalytic amounts of (-) sparteine serve as promoter for enantioselective carbolithiation of β-alkylated, non functionalized styrene.

Asymmetric Conjugate Addition to Unsaturated Chiral Amido Alcohols Using Grignard Reagents Co-ordinated with Tertiary Amines or DBU. Preparation of Optically Active 3-Substituted Carboxylic Acids and (S)-(-)-Citronellol

Optically active 3-substituted carboxylic acids and (S)-(-)-citronellol have been obtained by diastereoselective conjugate addition of Grignard reagents co-ordinated with 1,8-diazabicyclo-undec-7-ene (DBU) to chiral amidoalcohols derived from (S)-proline.

EFFICIENT ASYMMETRIC HYDROGENATIONS OF CAMPHOR-SULTAM-IMIDE-CONJUGATED ALKENES.

The trisubstituted olefinic bond of sultam-imides 2 was hydrogenated in the presence of Pd/C with >90percent diastereoface discrimination to give after saponification recovered auxiliary 7 and the β-substituted carboxylic acids 5 or 6 in high e.e..

Asymmetric Conjugate Addition of Grignard Reagents in the Presence of Tertiary Amines to α,β-Unsaturated Amides Derived from (S)-2-(1-Hydroxy-1-methylethyl)pyrrolidine or (S)-Prolinol

In the presence of tertiary amines, diastereoselective conjugate addition of Grignard reagents to α,β-unsaturated amides affords 3-substituted carboxylic acids of high enantiomeric excess (up to 89percent e.e.).

A FACILE ASYMMETRIC SYNTHESIS OF β-SUBSTITUTED ALKANOIC ACID. THE HIGHLY STEREOSELECTIVE MICHAEL ADDITION OF GRIGNARD REAGENTS TO α,β-UNSATURATED CARBOXYLIC AMIDES DERIVED FROM L-EPHEDRINE

The Michael addition of Grignard reagents to chiral α,β-unsaturated carboxylic amides derived from l-ephedrine affords highly optically active β-substituted alkanoic acids after acid hydrolysis.This high stereoselectivity is explained by considering the formation of rigid internal chelate complexes.