CAS 791616-55-2 (R)-(-)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate, min. 98% [(R)-TiPSY]

Synonyms

(S)-(+)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate; RD-0080; (11bR)-4-Hydroxy-2,6-bis(triphenylsilyl)dinaphtho-[2,1-d:1 inverted exclamation marka,2 inverted exclamation markaf]-1,3,2-dioxaphosphepin 4-oxide; Carreira SALDIPAC Ligand; (R)-(-)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate; (aS)-2,6-Bis(triphenylsilyl)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin 4-oxide; (R)-(-)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; (S)-3,3'-Bis(triphenylsilyl)-1,1'-binaphthalene-2,2'-diyl hydrogen phosphate; SC-44139; 929097-92-7;

IUPAC Name

(13-hydroxy-13-oxo-16-triphenylsilyl-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-10-yl)-triphenylsilane;

Molecular Weight

865.084g/mol

Molecular Formula

C56H41O4PSi2;

Canonical SMILES

C1=CC=C(C=C1)[Si](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC5=CC=CC=C5C6=C4OP(=O)(OC7=C6C8=CC=CC=C8C=C7[Si](C9=CC=CC=C9)(C1=CC=CC=C1)C1=CC=CC=C1)O;

InChI

InChI=1S/C56H41O4PSi2/c57-61(58)59-55-51(62(43-25-7-1-8-26-43,44-27-9-2-10-28-44)45-29-11-3-12-30-45)39-41-23-19-21-37-49(41)53(55)54-50-38-22-20-24-42(50)40-52(56(54)60-61)63(46-31-13-4-14-32-46,47-33-15-5-16-34-47)48-35-17-6-18-36-48/h1-40H,(H,57,58);

InChI Key

BDQOCXQVIFQJRK-UHFFFAOYSA-N;

Complexity

1320

Covalently-Bonded Unit Count

Exact Mass

864.228g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

864.228g/mol

Rotatable Bond Count

Topological Polar Surface Area

55.8A^2

Application

(R)-TiPSY serves as a high-purity chiral phosphoric acid catalyst employed in a variety of enantioselective reactions. Notably, it provides an effective approach for the organocatalytic reductive amination of heterocyclic amines, enabling the construction of protected primary amines with high stereoselectivity. This catalyst is instrumental in numerous significant reactions, such as the Biginelli and Biginelli-like reactions, and the asymmetric, three-component Povarov reaction with 2-hydroxystyrenes. It facilitates the production of structurally diverse cis-disubstituted tetrahydroquinolines with exceptional stereoselectivity. Additionally, (R)-TiPSY is part of a gold/chiral phosphoric acid system used for the synthesis of aromatic spiroacetals from salicylaldehydes, anilines, and alkynols, providing high yields and stereoselectivity. This product also supports the first highly enantioselective catalytic protocol for reductive coupling of ketones and hydrazones, with dual activation enabling reagent-controlled regioselectivity.

February 27, 2025

Outstanding Catalyst for Reductive Amination

I've used Alfa Chemistry's (R)-TiPSY in my lab for enantioselective organocatalytic reductive amination. It delivered exceptional stereoselectivity, significantly enhancing our synthesis of protected primary amines. Highly recommend for precise chiral synthesis!