(-)-Diisopinocampheyl Borane - CAS 21932-54-7
Category:
Main Product
Product Name:
(-)-Diisopinocampheyl Borane
Catalog Number:
21932-54-7
Synonyms:
bis[(1R,3R,4S,5R)-4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]boron; 21932-54-7; Bis((1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane; (-)-Diisopinocampheylborane; bis[(1R,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl]borane; PubChem18202
CAS Number:
21932-54-7
Molecular Weight:
286.30
Molecular Formula:
C20H35B
Quantity:
Data not available, please inquire.
COA:
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MSDS:
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Canonical SMILES:
[B](C1CC2CC(C1C)C2(C)C)C3CC4CC(C3C)C4(C)C
InChI:
InChI=1S/C20H34B/c1-11-15-7-13(19(15,3)4)9-17(11)21-18-10-14-8-16(12(18)2)20(14,5)6/h11-18H,7-10H2,1-6H3/t11-,12-,13+,14+,15-,16-,17-,18-/m1/s1
InChIKey:
MPQAQJSAYDDROO-VMAIWCPRSA-N
Chemical Structure
CAS 21932-54-7 (-)-Diisopinocampheyl Borane

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Reference Reading


1.(Diisopinocampheyl)borane-mediated reductive aldol reactions of acrylate esters: enantioselective synthesis of anti-aldols.
Allais C1, Nuhant P, Roush WR. Org Lett. 2013 Aug 2;15(15):3922-5. doi: 10.1021/ol401679g. Epub 2013 Jul 25.
The (diisopinocampheyl)borane promoted reductive aldol reaction of acrylate esters 4 is described. Isomerization of the kinetically formed Z(O)-enolborinate 5Z to the thermodynamic E(O)-enolborinate 5E via 1,3-boratropic shifts, followed by treatment with representative achiral aldehydes, leads to anti-α-methyl-β-hydroxy esters 9 or 10 with excellent diastereo- (up to ≥20:1 dr) and enantioselectivity (up to 87% ee). The results of double asymmetric reactions of 5E with several chiral aldehydes are also presented.
2.Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane.
Allais C1, Tsai AS, Nuhant P, Roush WR. Angew Chem Int Ed Engl. 2013 Dec 2;52(49):12888-91. doi: 10.1002/anie.201307302. Epub 2013 Oct 15.
On all fours: The title reaction with (Ipc)2 BH provides tetrasubstituted enolborinates which undergo aldol reactions with aldehydes to form products with all-carbon quaternary centers with exceptional diastereo- and enantioselectivity. A change to the substitution pattern of the starting amide leads to either diastereomer of the α-methyl-α-ethyl-β-hydroxy carboxamide (1 or 2).