112022-81-8 Usage
Description
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole is a complex organic compound with a unique structure that features a pyrrolidine ring fused to an oxazaborole ring. It is characterized by its colorless to yellow liquid appearance and is known for its application as a catalyst in various chemical reactions.
Uses
Used in Asymmetric Reduction:
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole is used as an oxazaborolidine catalyst for the asymmetric reduction of prochiral ketones. This application is significant in the synthesis of enantiomerically pure compounds, which are crucial in the pharmaceutical industry for the development of drugs with fewer side effects.
Used in Enantioselective Synthesis:
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole is also utilized in the enantioselective synthesis of various chiral molecules, such as α-hydroxy acids, α-amino acids, C2-symmetrical ferrocenyl diols, and propargyl alcohols. The enantioselective synthesis is essential for creating biologically active molecules with specific properties, which are vital in the fields of pharmaceuticals, agrochemicals, and materials science.
Used in Suzuki Reaction:
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole is employed in the Suzuki reaction, a widely used cross-coupling reaction in organic chemistry. This reaction allows the formation of carbon-carbon bonds, which are fundamental in the construction of complex molecular structures. The use of this compound as a catalyst in the Suzuki reaction contributes to the development of new synthetic routes and the production of advanced materials and pharmaceuticals.
Reaction
Convenient catalyst for the enantioselective borane reduction of ketones at ambient temperatures.
Asymmetric synthesis of α-chiral hydroxyalkylphosphines via a catalytic, enantioselective reduction of acylphosphines.
Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: Stereospecific formation of diarylalkanes and triarylmethanes.
Enantioselective reduction of prochiral ketones with NaBH4/Me2SO4/(S)-Me-CBS.
Check Digit Verification of cas no
The CAS Registry Mumber 112022-81-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,2,0,2 and 2 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 112022-81:
(8*1)+(7*1)+(6*2)+(5*0)+(4*2)+(3*2)+(2*8)+(1*1)=58
58 % 10 = 8
So 112022-81-8 is a valid CAS Registry Number.
InChI:InChI=1/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
112022-81-8Relevant articles and documents
An enantioselective approach to cytotoxic norcalamenenes via electron-transfer-driven benzylic umpolung of an arene tricarbonyl chromium complex
Schmalz, Hans-Guenther,Kiehl, Oliver,Korell, Ursula,Lex, Johann
, p. 1851 - 1855 (2003)
An efficient enantioselective total synthesis of (R)-1-isopropenyl-6-methoxy-7-methyl-1,2,3,4-tetrahydronaphthalene, the dehydro-analog of the cytotoxic norsesquiterpene (R)-7-demethyl-2-methoxycalamenene, was achieved in seven steps starting from 6-methoxytetralone. The synthesis exploits the specific reactivity and stereochemistry of planar chiral η6-arene-Cr(CO)3 complexes. In a key step, a Cr(CO)3-complexed benzylic anion, regioselectively generated by means of electron- transfer-driven benzylic umpolung, is diastereoselectively alkylated with acetyl chloride.
Stereospecific, Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Allylic Pivalates to Deliver Quaternary Stereocenters
Cobb, Kelsey M.,Rabb-Lynch, Javon M.,Hoerrner, Megan E.,Manders, Alex,Zhou, Qi,Watson, Mary P.
supporting information, p. 4355 - 4358 (2017/08/23)
Recognizing the importance of all-carbon, quaternary stereocenters in complex molecule synthesis, a stereospecific, nickel-catalyzed cross-coupling of allylic pivalates with arylboroxines to deliver products equipped with quaternary stereocenters and internal alkenes was developed. The enantioenriched allylic pivalate starting materials are readily prepared, and a variety of functional groups can be incorporated on both the allylic pivalate and the arylboroxine. Additional advantages include the use of a commercially available and air-stable Ni(II) salt and BISBI ligand, mild reaction conditions, and high yields and ee's. The observed stereoinversion of this reaction is consistent with an open transition state in the oxidative addition step.
Enantioselective catalytic desymmetrization of maleimides by temporary removal of an internal mirror plane and stereoablative over-reduction: Synthesis of (R)-pyrrolam A
Marsh, Barrie J.,Adams, Harry,Barker, Mike D.,Kutama, Ibrahim U.,Jones, Simon
supporting information, p. 3780 - 3783 (2014/08/05)
A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product pyrrolam A.