328123-63-3

Upstream product

• 153489-62-4 (R_a)-4-cyclohexyl-2,3-butadien-1-ol 
• 2043-61-0 cyclohexanecarbaldehyde 
• 109907-84-8 1-cyclohexylbuta-2,3-dien-1-ol 
• 97563-45-6 1-cyclohexylprop-2-yn-1-ol 
• 1191-99-7 2,3-dihydro-2H-furan 
• 131929-90-3 cyclohexyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

OPTICALLY ACTIVE AXIALLY CHIRAL ALPHA-ALLENIC ALCOHOL, SYNTHESIS METHOD AND USE THEREOF

The present invention relates to an optically active axially chiral α-allenic alcohol, a synthetic method and use thereof. A method of preparing a high optically active chiral α-allenic alcohol by using propargyl alcohol, aldehyde and chiral α,α-diphenyl-L-prolinol under the protection of tert-butyldimethylsilyl with a mediator zinc bromide. The axially chiral α-allenic alcohol has the structural formula (I). The method of the present invention has the following advantages: the synthesis route is short, operations are simple, raw materials are readily available, separation and purification are convenient, the substrate has high generality, the total yield is high, and enantioselectivity and diastereoselectivity are high. The high optically active axially chiral α-allenic alcohol synthesized by adopting the method of the present invention can conveniently synthesize 2,5-dihydrofuran compounds having central chirality via complete chirality transfer, and at the same time can further be used to synthesize axially chiral allenic amine and allenic malonate compounds without reacemization.

Tert-butyldimethylsilyl-directed highly enantioselective approach to axially chiral α-allenols

A highly efficient and enantioselective synthesis of axially chiral α-allenols was realized in practical yields with 96-99 % ee or de from TBS-protected propargylic alcohols, aldehydes, and a commercially available, inexpensive, chiral, secondary amine (S)-α,α-diphenylprolinol or its enantiomer followed by desilylation. The easily removable TBS group not only acts as a protecting group, but also as a possible sterically directing group for the excellent enantioselectivity and in situ prevention of possible allene racemization. Copyright

Chiral silver phosphate-catalyzed cycloisomeric kinetic resolution of α-allenic alcohols

A kinetic resolution of α-allenic alcohols is realized through chiral silver phosphate-catalyzed cycloisomerization with high stereoselectivity (selectivity factor up to 189) and tolerance of a variety of functional groups. A mechanistic model is proposed to interpret the origin of the high stereoselectivity and broad substrate scope.

A dramatic switch of enantioselectivity in asymmetric heck reaction by benzylic substituents of ligands

A series of benzylic substituted P,N-ligands 1 and 2 have been synthesized. The Pd-complexes of these ligands show high catalytic activity and enantioselectivity in catalyzing the asymmetric Heck reaction. A dramatic switch in enantioselectivity is realized using ligands with and without substituents at the benzylic position of the ligand. Ligands 1 with H as the substituents offer products in (R)-configuration while ligands 2 with the methyl as substituents result in (S)-configuration products. In most cases high enantioselectivities are achieved. Density functional theory calculations on the reaction mechanism as well as X-ray analysis of 1a-PdCl2 and 2a-PdCl2 complexes provide a rational explanation for the above observations.