665290

(S,S,S)-(+)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a:3,4-a′]dinaphthalen-4-yl)bis(1-phenylethyl)amine

97%

• Synonym(s): (+)-N,N-Bis[(1S)-1-phenylethyl]- dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin- 4-amine, (11bR)
• Empirical Formula (Hill Notation): C₃₆H₃₀NO₂P
• CAS Number: 380230-02-4
• Molecular Weight: 539.60
• MDL number: MFCD04117688
• UNSPSC Code: 12352005
• PubChem Substance ID: 24884726
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 97%
• form: solid
• mp: 88-89 °C
• functional group: amine; phenyl
• SMILES string: C[C@H](N([C@@H](C)c1ccccc1)P2Oc3ccc4ccccc4c3-c5c(O2)ccc6ccccc56)c7ccccc7
• InChI: 1S/C36H30NO2P/c1-25(27-13-5-3-6-14-27)37(26(2)28-15-7-4-8-16-28)40-38-33-23-21-29-17-9-11-19-31(29)35(33)36-32-20-12-10-18-30(32)22-24-34(36)39-40/h3-26H,1-2H3/t25-,26-/m0/s1
• InChI key: LKZPDRCMCSBQFN-UIOOFZCWSA-N

Description

Application

DSM MonoPhos Family of Highly Efficient Privileged Ligands

Chiral phosphoramidite ligand used in a highly enantioselective copper-catalyzed conjugate addition of diakylzincs to a variety of Michael acceptors.[1][2][3] Also used in a palladium-catalyzed diethylzinc mediated umpolung allylation.[4]

The product may be used as a ligand in:

• Iridium-catalyzed allylic etherification of acyclic, achiral allylic carbonates with potassium silanolates to form chiral allylic alcohols.[5]
• Palladium-catalyzed asymmetric allylic cyclisation of N-tosyl and N-benzyl carbonates to form the corresponding pyrrolidine and piperidine derivatives, respectively.[6]
• Intramolecular iridium-catalyzed allylic cyclizationof (E)-allylic methyl carbonates to form 2,5-trans/cis pyrrolidine derivatives.[7]

Features and Benefits

Advantages of the MonoPhos^® ligands:[8]

• Superior enantiocontrol in numerous transformations
• High activities at low catalyst loadings
• Hydrogenations under low-pressure conditions

Legal Information

Sold under license from DSM for research purposes only.

MonoPhos is a registered trademark of DSM IP Assets B.V.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)