777067-26-2

Upstream product

• 905984-16-9 lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide 
• 10024-74-5 (R,R)-N,N-bis-(1-phenylethyl)amine 

Downstream Products

• 882992-52-1 C₄₈H₃₈NO₂P 
• 1309474-50-7 1,1-bis(hex-1-yn-1-yl)-N,N-bis((R)-1-phenylethyl)phosphinamine 
• 1021439-60-0 (5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl)-2,2'-diyl (R)-bis(1-phenylethyl)-phosphoramidite 
• 1190295-44-3 (3aS)-2-phenyl-N,N-bis[(R)-1-phenylethyl]-hexahydro-1H-pyrrolo[1,2-c][1,3,2]diazaphosphol-1-amine 
• 1190295-44-3 (3aS)-2-phenyl-N,N-bis[(R)-1-phenylethyl]-hexahydro-1H-pyrrolo[1,2-c][1,3,2]diazaphosphol-1-amine 
• 500103-26-4 O,O'-(1,1'-biphenyl-2,2'-diyl)-N,N'-bis[(S,S)-1-phenyl-ethyl]phosphoramidite 

Relevant academic research and scientific papers

Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to cyclic enones with spirocyclic phosphoramidite ligands

A series of spirocyclic phosphoramidite ligands 6-9 with different substituents on the amine moiety were synthesized from the chiral spirocyclic diol (R)-5. These monodentate ligands have been applied in copper-catalyzed conjugate addition of diethylzinc

Enantioselective Alkoxycyclization of 1,6-Enynes with Gold(I)-Cavitands: Total Synthesis of Mafaicheenamine C

Chiral gold(I)-cavitand complexes have been developed for the enantioselective alkoxycyclization of 1,6-enynes. This enantioselective cyclization has been applied for the first total synthesis of carbazole alkaloid (+)-mafaicheenamine C and its enantiomer, establishing its configuration as R. The cavity effect was also evaluated in the cycloisomerization of dienynes. A combination of experiments and theoretical studies demonstrates that the cavity of the gold(I) complexes forces the enynes to adopt constrained conformations, which results in the high observed regio- and stereoselectivities.

SPHENOL, A New Chiral Framework for Asymmetric Synthesis

Privileged chiral catalysts have found tremendous applications and thus immensely advanced asymmetric synthesis in the past few decades. However, truly privileged chiral frameworks are still extremely limited. Thus, the search for and development of new v

Concise synthesis and applications of enantiopure spirobiphenoxasilin-diol and its related chiral ligands

The development of chiral architectures for chiral ligand and catalyst discovery is essential for asymmetric catalysis. Herein, we report the concise synthesis of a Si-centered spirocyclic skeleton, spirobiphenoxasilin-diol (SPOSiOL), and its derived chiral ligands. Using the chemical resolution method, the optical SPOSiOL could be obtained in high yield on a gram scale. Preliminary studies indicated that this ligand scaffold has great potential in transition metal-catalyzed asymmetric reactions. This finding further highlights that the Si-centered spirocyclic scaffolds are of great value in asymmetric catalysis. This journal is

Enantioselective Synthesis of 3,3′-Diaryl-SPINOLs: Rhodium-Catalyzed Asymmetric Arylation/BF3-Promoted Spirocyclization Sequence

The enantioselective synthesis of a series of C2-symmetric 3,3′-diarylated 1,1′-spirobiindane-7,7′-diols (3,3′-diaryl-SPINOLs) was developed by sequential Rh-catalyzed twofold asymmetric conjugate arylation/BF3-promoted diastereoselective spirocyclization (>20:1 d.r. and >99 % ee for all examples). Some phosphoramidite ligands were prepared from the 3,3′-Ph-SPINOL and applied to several catalytic asymmetric reactions, and the 3,3′-diarylated ligands showed higher enantioselectivities than the privileged nonsubstituted ligands.

Asymmetric synthesis method for 3,3'-diaryl substituted chiral spiro bisphenol compound

The invention discloses an asymmetric synthesis method for a 3,3'-diaryl substituted chiral spiro bisphenol compound. The method comprises the steps that acetone serves as a raw material and is subjected to condensation reaction with substituted benzaldeh

Investigating the Enantiodetermining Step of a Chiral Lewis Base Catalyzed Bromocycloetherification of Privileged Alkenes

The development of catalytic, enantioselective halofunctionalizations of unactivated alkenes has made significant progress in recent years. However, the identification of generally applicable catalysts for wide range of substrates has yet to be realized.

Synthesis and application of a new chiral monodentate spiro phosphoramidite ligand based on hexamethyl-1,1′-spirobiindane backbone in asymmetric hydroamination/arylation of alkenes

The design and synthesis of a new chiral monodentate spiro phosphoramidite ligand based on a hexamethyl-1,1′-spirobiindane scaffold has been accomplished. The ligand could serve as an elegant chiral monodentate ligand in the Pd-catalyzed asymmetric hydroamination/arylation of alkenes leading to chiral imidazolidin-2-ones with good enantioselectivities.

Chiral Cyclohexyl-Fused Spirobiindanes: Practical Synthesis, Ligand Development, and Asymmetric Catalysis

1,1′-Spirobiindane has been one type of privileged skeleton for chiral ligand design, and 1,1′-spirobiindane-based chiral ligands have demonstrated outstanding performance in various asymmetric catalysis. However, the access to enantiopure spirobiindane is quite tedious, which obstructs its practical application. In the present article, a facile enantioselective synthesis of cyclohexyl-fused chiral spirobiindanes has been accomplished, in high yields and excellent stereoselectivities (up to >99% ee), via a sequence of Ir-catalyzed asymmetric hydrogenation of α,α′-bis(arylidene)ketones and TiCl4 promoted asymmetric spiroannulation of the hydrogenated chiral ketones. The protocol can be performed in one pot and is readily scalable, and has been utilized in a 25 g scale asymmetric synthesis of cyclohexyl-fused spirobiindanediol (1S,2S,2′S)-5, in >99% ee and 67% overall yield for four steps without chromatographic purification. Facile derivations of (1S,2S,2′S)-5 provided straightforward access to chiral monodentate phosphoramidites 6a-c and a tridentate phosphorus-amidopyridine 11, which were evaluated as chiral ligands in several benchmark enantioselective reactions (hydrogenation, hydroacylation, and [2 + 2] reaction) catalyzed by transition metal (Rh, Au, or Ir). Preliminary results from comparative studies showcased the excellent catalytic performances of these ligands, with a competency essentially equal to the corresponding well-established privileged ligands bearing a regular spirobiindane backbone. X-ray crystallography revealed a close resemblance between the structures of the precatalysts 20 and 21 and their analogues, which ultimately help to rationalize the almost identical stereochemical outcomes of reactions catalyzed by metal complexes of spirobiindane-derived ligands with or without a fused cyclohexyl ring on the backbone. This work is expected to stimulate further applications of this type of readily accessible skeletons in development of chiral ligands and functional molecules.

Palladium-catalyzed, asymmetric Mizoroki-Heck reaction of benzylic electrophiles using phosphoramidites as chiral ligands

We report herein the first examples of asymmetric Mizoroki-Heck reactions using benzyl electrophiles. A new phosphoramidite was identified to be an effective chiral ligand in the palladium-catalyzed reaction. The reaction is compatible with polar functional groups and can be readily scaled up. Several cyclic olefins worked well as olefin components. Thirty-one examples are included.