CAS 157488-65-8 (R)-(-)-(3,5-Dioxa-4-phosphacyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)dimethylamine

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

Exact Mass

359.108g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

359.108g/mol

Rotatable Bond Count

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.