CAS 112022-81-8 (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine

Synonyms

AKOS015840981; (S)-1-methyl-3,3-diphenyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole; MFCD00078439; (S)- Methyl-CBS-oxazaborolidine; ZINC169743318; (S)-tetrahydro-1-methyl-3,3-diphenyl-1 H,3 H-pyrrolo[1,2-c][1,3,2] oxazaborole; (S)-1-methyl-3,3-diphenylhexahydropyrrolo-[1,2-c][1,3,2]oxazaborole; (S)-tetrahydro-1-methyl-3,3-diphenyl-1 H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole; (S)-Me-CBS; Corey catalyst;

IUPAC Name

(3aS)-1-methyl-3,3-diphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole;

Molecular Weight

277.174g/mol

Molecular Formula

C18H20BNO;

Canonical SMILES

B1(N2CCCC2C(O1)(C3=CC=CC=C3)C4=CC=CC=C4)C;

InChI

InChI=1S/C18H20BNO/c1-19-20-14-8-13-17(20)18(21-19,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17H,8,13-14H2,1H3/t17-/m0/s1;

InChI Key

VMKAFJQFKBASMU-KRWDZBQOSA-N;

Storage

Refrigerator

Complexity

344

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

277.164g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

277.164g/mol

Rotatable Bond Count

Topological Polar Surface Area

12.5A^2

Application

(S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine serves primarily as an efficient oxazaborolidine catalyst. Its primary purpose lies in facilitating the asymmetric reduction of prochiral ketones, a critical process in creating enantiomerically pure compounds. This catalyst also plays a crucial role in the enantioselective synthesis of various complex molecules such as α-hydroxy acids, α-amino acids, and C2-symmetrical ferrocenyl diols. In addition, it is utilized in propargyl alcohols synthesis and operates effectively in anhydrous environments to catalyze 'CBS' reduction reactions, including the Suzuki reaction. Furthermore, it provides a convenient solution for the enantioselective borane reduction of ketones at ambient temperatures. Its application extends to the catalytic, enantioselective reduction of acylphosphines for the asymmetric synthesis of α-chiral hydroxyalkylphosphines. Additionally, it assists in nickel-catalyzed cross-couplings, achieving the stereospecific formation of complex molecules such as diarylalkanes and triarylmethanes. This catalyst's versatility is also evident in the enantioselective reduction of prochiral ketones when used in combination with NaBH4/Me2SO4.

February 19, 2025

Essential Catalyst for Asymmetric Synthesis

I've used (S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine from Alfa Chemistry in asymmetric ketone reductions. Its precise catalysis delivered excellent enantioselectivity for my research, significantly impacting the synthesis of α-hydroxy acids and propargyl alcohols. Highly recommended!