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112022-81-8 - (S)-2-Methyl-CBS-oxazaborolidine monohydrate, 94% - (S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole - L09219 - Alfa Aesar

L09219 (S)-2-Methyl-CBS-oxazaborolidine monohydrate, 94%

CAS Number
112022-81-8
Synonyms
(S)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole

Size Price ($) Quantity Availability
250mg 125.00
1g 395.00
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(S)-2-Methyl-CBS-oxazaborolidine monohydrate, 94%

MDL
MFCD00078439

Chemical Properties

Formula
C18H20BNO•H2O
Formula Weight
295.19 (277.17anhy)
Melting point
115-121°

Literature References

Air-stable solid prepared by a modification of Corey's procedure, on which his literature results were based. For anhydrous reagent, see (S)-2-Methyl-CBS-oxazaborolidine, L14583.

/n

Catalyst for the CBS (Corey, Bakshi, Shibata) reduction of prochiral ketones with borane-THF, with high enantioselectivity (see (S)-(-)-ɑ,ɑ-Diphenyl­prolinol, L09217): J. Am . Chem. Soc., 109, 7925 (1987):

/n

For successful use of this system in a scaled up asymmetric synthesis of the antiarrythmia agent d-Sotalol, see: Org. Process Res. Dev., 1. 176 (1997). For use in enantioselective reduction of ketones containing heteroatoms, see: Tetrahedron Lett., 34, 785 (1993). For the asymmetric reduction of ɑ-ketoimines, see: Tetrahedron Lett., 35, 5551 (1994).

/n

For reviews of oxazaborolidines as enantioselective catalysts, see: Angew. Chem. Int. Ed., 31, 729 (1992); 37, 1986 (1998); Tetrahedron: Asymmetry, 3, 1475 (1992).

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For reviews of the asymmetric reduction of ketones, see: Synthesis, 605 (1992); Chem. Ind. (London), 552 (1994).

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Other References

Beilstein
8492123
Harmonized Tariff Code
2934.99
TSCA
No

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