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- (R)-(-)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)dimethylamine
(R)-(-)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)dimethylamine
PRICE INQUIRYCatalog Number
ACM157488658-3
Product Name
(R)-(-)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)dimethylamine
Structure
![{[CurrentData.Name]}](https://resource.alfachemic.com/structure/157488-65-8.gif)
CAS
157488-65-8
Synonyms
(R)-(-)-(3,5-DIOXA-4-PHOSPHACYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE; 9699AA; (S)-(+)-(3,5-Dioxa-4-phospha-cyclohepta[2,1-a; FT-0701641; 3,4-a']dinaphthalen-4-yl)dimethylamine; A116071; A116070; 4CH-018602; SY226298; AX8210337;
IUPAC Name
N,N-dimethyl-12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-amine;
Molecular Weight
359.365g/mol
Molecular Formula
C22H18NO2P;
Canonical SMILES
CN(C)P1OC2=C(C3=CC=CC=C3C=C2)C4=C(O1)C=CC5=CC=CC=C54;
InChI
InChI=1S/C22H18NO2P/c1-23(2)26-24-19-13-11-15-7-3-5-9-17(15)21(19)22-18-10-6-4-8-16(18)12-14-20(22)25-26/h3-14H,1-2H3;
InChI Key
QCHAVHXSBZARBO-UHFFFAOYSA-N;
Complexity
461
Covalently-Bonded Unit Count
1
Exact Mass
359.108g/mol
H-Bond Acceptor
3
Heavy Atom Count
26
Monoisotopic Mass
359.108g/mol
Rotatable Bond Count
1
Topological Polar Surface Area
29.5A^2
Application
The purpose of (R)-(-)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)dimethylamine is to serve as a highly efficient privileged ligand in various enantioselective catalytic reactions. This ligand is integral in rhodium-catalyzed hydrogenation of substituted olefins, including N-acetyldihydroamino acids, enamides, and unsaturated acids. It is also utilized in iridium-catalyzed allylic substitution of allyl acetates with a single substituent in the 1 or 3 position. Additionally, it plays a key role in rhodium-catalyzed, amide-directed asymmetric hydroboration, as well as in the asymmetric conjugate addition of aryl boronic acids to dihydronitronaphthalenes. Furthermore, the ligand is used in rhodium-catalyzed asymmetric intramolecular 1,4 addition, contributing to its versatility and efficacy in asymmetric synthesis.
March 29, 2025
Reliable Ligand for Advanced Asymmetric Catalysis
I used this ligand in a rhodium-catalyzed hydrogenation of substituted olefins. It was efficient and enhanced enantioselectivity, crucial for my research on N-acetyldihydroamino acids. Highly recommended for precision-driven experiments.
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