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Sku SC15-1366_100_MG
US-Strem
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Product Information

Product Name
(11bR)-2,6-Bis3,5-bis(trifluoromethyl)phenyl-4-hydroxy-4-oxide-dinaphtho2,1-d:1',2'-f1,3,2dioxaphosphepin, 98%, (99% ee)
Brand Name
US-Strem
Product Number
15-1366
CAS
791616-62-1
Certificate of Analysis (COA)​
COA not found

General Information

PubChem CID
11468389
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(15),2(11),3,5,7,9,16,18,20,22-decaene 13-oxide
InChI Key
DQORDVSQWPKAQJ-UHFFFAOYSA-N
SMILES
C1=CC=C2C(=C1)C=C(C3=C2C4=C(C(=CC5=CC=CC=C54)C6=CC(=CC(=C6)C(F)(F)F)C(F)(F)F)OP(=O)(O3)O)C7=CC(=CC(=C7)C(F)(F)F)C(F)(F)F

Application

Technical Notes:
1.Reductive Amination Reaction: The first enantioselective organocatalytic reductive amination reaction has been accomplished.
2.Mannich Reaction: In the presence of a catalytic amt. of the phosphoric acid, anti-selective Mannich
reactions of cyclic ketones with a wide scope of aldimines were obtained.
3.The diastereoselectively switchable enantioselective trapping of protic carbamate ammonium ylides with imines is reported. The Rh2( )Ac)4 and chiral Brønsted acid cocatalyzed three-component Mannich-type reaction of a diazo compound, a carbamate, and an imine provides rapid and efficient access to both syn- and anti-a -substituted a, ß-diamino acid de rivatives .
4.Protonation: A catalytic asymmetric protonation of ketene dithioacetals is described. Various racemic a-aryl hyd rocoumarin derivatives are transformed into e nantioenriched dithioacetal- protected hydrocoumarins in
the presence of a chiral Brønsted acid catalyst.
5.Povarov Cyclization: Tetrahydroquinolines containing two quaternary stereogenic centers were
synthesized with excellent ee and dr via a four-component cyclization reaction catalyzed by a chiral
phosphoric acid.
6.Pictet-Spengler Reaction: ß-Carbolines could be synthesized with good enantioselectivity by the Pictet- Spengler reaction catalyzed by a chiral binol-derived Bronsted acid .
7.In the glycosylation of racemic alcohols with 1 using the chiral phosphoric acid as an activator, one
enantiomer of the racemic alcohol selectively reacts with 1 to give the corresponding glycoside with good to excellent a/ß-stereo- and diastereoselectivity in high yield.

References Data Source From Pubchem

Enantioselective Addition of Oxonium Ylides to ortho-Quinomethanes with Rhodium(II)

Publication Name: Science of Synthesis
Publication Date: 2019

Chiral Pyrophosphoric Acid Catalysts for the para-Selective and Enantioselective Aza-Friedel–Crafts Reaction of Phenols

Publication Name: Synthesis
Publication Date: 2018-08-22
DOI: 10.1055/s-0037-1610250

Asymmetric Cycloetherification by Bifunctional Organocatalyst

Publication Name: Synthesis
Publication Date: 2018-06-26
DOI: 10.1055/s-0036-1591592

Spirocyclic Orthoesters, Orthothioesters and Orthoaminals in the Synthesis and Structural Modification of Natural Products

Publication Name: Synthesis
Publication Date: 2016-12-30
DOI: 10.1055/s-0036-1588339

Enantioselective amine alpha-functionalization via palladium-catalysed C-H arylation of thioamides.

Publication Name: Nature Chemistry
Publication Date: 2016-10-03
DOI: 10.1038/nchem.2619