196940-65-5

Upstream product

• 100-52-7 benzaldehyde 
• 257629-47-3 5-hydroxypentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 
• 196940-78-0 5-bromopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 

Downstream Products

• 58647-76-0 exo-6-phenylbicyclo[3.1.0]hexane 
• 196940-67-7 (-)-(1R,2S)(Z)-2-benzylcyclopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 
• 196940-71-3 (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 
• 135357-02-7 (-)-(1R,2S)-2-benzylcyclopentanol 
• 135356-99-9 (-)-(1R,2S)-2-benzylcyclopentyl acetate 
• 196940-77-9 (-)-(1R,2R)-2-[(S)-(dimethylphenylsilyl)(phenyl)methyl]cyclopentanol 

Relevant academic research and scientific papers

(-)-sparteine-mediated asymmetric intramolecular carbolithiation of alkenes: Synthesis of enantiopure cyclopentanes with three consecutive stereogenic centers

An asymmetric intramolecular carbolithiation reaction was developed by combining the (-)-sparteine-mediated enantiotopos-differentiating deprotonation and the anionic 5-exo-trig cyclization. Achiral 6-phenylhex-5- enyl carbamates were efficiently cyclized furnishing regio-, diastereo- (dr >99:1), and enantioselectively (er >98:2) 1,2-trans-substituted cyclopentanes. The intermediate primary benzylic lithium-carbanion pairs were - in spite of their configurative lability - diastercoselectively substituted by versatile electrophiles creating a third consecutive stereogenic center. Additionally, some 4-functionalized 6-phenylhex-5-enyl carbamates were also cyclized in high yield to provide enantiomerically pure cyclopentanes incorporating three adjacent stereogenic centers.