295328-86-8

Upstream product

• 107-11-9 1-amino-2-propene 
• 295328-90-4 (1R,4R)-1,4-bis(methanesulfonyloxy)-1,4-diphenylbutane 
• 70-11-1 α-bromoacetophenone 
• 495-71-6 phenacylacetophenone 
• 214280-56-5 (+)-(1R,4R)-1,4-diphenylbutane-1,4-diol 
• 2085-90-7 1,4-diphenyl-1,4-butanediol 

Downstream Products

• 295328-85-7 (2S,5S)‐diphenylpyrrolidine 
• 155155-73-0 (R,R)-2,5-diphenylpyrrolidine 

Relevant academic research and scientific papers

Enantioselective Stetter Reactions Catalyzed by Bis(amino)cyclopropenylidenes: Important Role for Water as an Additive

The first highly enantioselective intermolecular Stetter reaction using simple enones is reported. A series of novel chiral BAC structures were designed and prepared. They were tested in the Stetter reaction with simple aldehydes and enones. The products were generated in excellent yields and enantioselectivities (up to 94% ee). Surprisingly, a substoichiometric amount of water was crucial to obtain high enantioselectivities. Chiral BACs were also shown to catalyze 1,6-conjugate addition reactions with paraquinone methides enantioselectively.

A general, enantioselective synthesis of 2-substituted thiomorpholines and thiomorpholine 1,1-dioxides

In the course of our drug discovery programs, we had need to access chiral, 2-substituted thiomorpholines and their oxidized congeners, thiomorpholine 1,1-dioxides. Here, we disclose a high-yielding, general protocol for the enantioselective synthesis of

A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis

A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functionalized aziridines in 50-73% overall yields and 88-94% ee, and azetidines in 22-32% overall yields and 84-92% ee. Moreover, we developed a scalable and cost-effective route to the key organocatalyst (54% overall yield, >95% dr).

Mukaiyama-Michael reactions with acrolein and methacrolein: A catalytic enantioselective synthesis of the C17-C28 fragment of pectenotoxins

Enantioselective iminium-catalyzed reactions with acrolein and methacrolein are rare. A catalytic enantioselective Mukaiyama-Michael reaction that readily accepts acrolein or methacrolein as substrates, affording the products in good yields and 91-97% ee, is presented. As an application of the methodology, an enantioselective route to the key C17-C28 segment of the pectenotoxin using the Mukaiyama-Michael reaction as the key step is described.

Efficient preparation of optically pure C2-symmetrical cyclic amines for chiral auxiliary

Optically pure C2-symmetrical amines were efficiently synthesized from the corresponding diols obtained from the enantioselective borohydride reduction of the diketones catalyzed by the optically active β-ketoiminato cobalt(II) complex.

A simple enantioselective preparation of (2S,5S)-2,5-diphenylpyrrolidine and related diaryl amines

A short efficient catalytic asymmetric route to the preparation of C2-symmetric diaryl cyclic amines is described. Copyright (C) 2000 Elsevier Science Ltd.