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Upstream product

• 1009080-89-0 ((S)-1-((S)-cyclohexenyl-1-phenylprop-2-ynyl)pyrrolidin-2-yl)methanol 
• 1422177-19-2 (S)-1-((S)-3-(cyclohex-1-en-1-yl)-1-phenylprop-2-yn-1-yl)-2-(pyrrolidin-1-ylmethyl)pyrrolidine 
• 51207-66-0 (S)-2-(1-pyrrolidinylmethyl)pyrrolidine 
• 100-52-7 benzaldehyde 
• 931-49-7 1-ethenylcyclohexene 

Relevant academic research and scientific papers

Highly Enantioselective Synthesis Using Prolinol as a Chiral Auxiliary: Silver-Mediated Synthesis of Axially Chiral Vinylallenes and Subsequent (Hetero)-Diels-Alder Reactions

Using (S)-prolinol as a chiral auxiliary, axially chiral vinylallenes with excellent enantiopurity (up to >99% enantiomeric excess (ee)) were readily prepared from optically pure propargylamines in the presence of AgNO3 under microwave irradiation. Subsequent (hetero)-Diels-Alder reaction of these axially chiral vinylallenes with azodicarboxylates or maleimides on water demonstrates excellent axial-to-point chirality transfer (up to 99% ee).

Enantioselective synthesis of both enantiomers of chiral allenes using chiral N-methylcamphanyl piperazine templates

The reaction of unsubstitued camphanyl-piperazine 4 with ZnCl2, phenylacetylene, and benzaldehyde in toluene gave the corresponding dipropargylamine (i.e., 15) with opposite configurations at the newly formed stereogenic centres, which, upon re

Copper(I) halide promoted diastereoselective synthesis of chiral propargylamines and chiral allenes using 2-dialkylaminomethylpyrrolidine, aldehydes, and 1-alkynes

Copper bromide promoted reactions of aldehydes, 1-alkynes, and chiral 2-dialkylaminomethylpyrrolidine at 25 C give the corresponding chiral propargylamine derivatives in up to 96% yield and 99:1 dr that are readily converted to the corresponding disubstit

Highly enantioselective synthesis of chiral allenes by sequential creation of stereogenic center and chirality transfer in a single pot operation

Chiral allenes are readily accessed in a single pot operation in the reaction of terminal alkynes, aldehydes, chiral secondary amines, and zinc halides in good yields (up to 77% yield) and excellent enantioselectivities (up to 99% ee) in toluene at 120 °C. The reaction proceeds through initial formation of chiral propargylamine intermediates with creation of a new stereogenic center and subsequent chirality transfer via an intramolecular hydride shift to produce chiral allenes with high enantiomeric purities.

Silver(i)-mediated highly enantioselective synthesis of axially chiral allenes under thermal and microwave-assisted conditions

Silver(i) salts mediated stereospecific transformation of optically active propargylamines to axially chiral allenes with excellent enantioselectivities (17 examples with 96-99% ee; one substrate with 91% ee) without subsequent racemization.