(11bR)-2,6-Bis[3,5-bis(trifluoromethyl)phenyl]-8,9,10,11,12,13,14,15-octahydro-4-hydroxy-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, 98%, (99% ee)|15-1376|1011465-24-9

(11bR)-2,6-Bis[3,5-bis(trifluoromethyl)phenyl]-8,9,10,11,12,13,14,15-octahydro-4-hydroxy-4-oxide-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, 98%, (99% ee)

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Product Information

Product Name
(11bR)-2,6-Bis3,5-bis(trifluoromethyl)phenyl-8,9,10,11,12,13,14,15-octahydro-4-hydroxy-4-oxide-dinaphtho2,1-d:1',2'-f1,3,2dioxaphosphepin, 98%, (99% ee)
Brand Name
US-Strem
Product Number
15-1376
CAS
1011465-24-9
Certificate of Analysis (COA)​
COA not found

General Information

PubChem CID
23110722
IUPAC Name
10,16-bis3,5-bis(trifluoromethyl)phenyl-13-hydroxy-12,14-dioxa-13λ5-phosphapentacyclo13.8.0.02,11.03,8.018,23tricosa-1(23),2,8,10,15,17-hexaene 13-oxide
InChI Key
INSXQFYWKHPSHX-UHFFFAOYSA-N
SMILES
C1CCC2=C3C4=C5CCCCC5=CC(=C4OP(=O)(OC3=C(C=C2C1)C6=CC(=CC(=C6)C(F)(F)F)C(F)(F)F)O)C7=CC(=CC(=C7)C(F)(F)F)C(F)(F)F

Application

Technical Notes:
1. The preparation of binaphthol monophosphoric acid derivatives.
2.Sigmatropic Rearrangements: Used in the organocatalytic aryl-aryl bond-forming process for the regio- and atroposelective synthesis of 2,2'-diamino-1,1'-binaphthalenes (BINAMs).In the presence of catalytic amounts of axially chiral phosphoric acids, achiral N,N'-binaphthyl hydrazines undergo a facile 3,3-
sigmatropic rearrangement to afford enantiomerically enriched BINAM derivatives in good to excellent yield.
References:
1: JP4725757E81038877 u86274745,12000-3-21.

References Data Source From Pubchem

Asymmetric Benzidine Rearrangement
Publication Name: Synfacts
Publication Date: 2013-08-19
DOI: 10.1055/s-0033-1339626