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445940

Sigma-Aldrich

(−)-Bis[(S)-1-phenylethyl]amine hydrochloride

97%

Synonym(s):
[S-(R*,R*)]-(−)-Bis(-α-methylbenzyl)amine hydrochloride
Linear Formula:
[C6H5CH(CH3)]2NH·HCl
CAS Number:
Molecular Weight:
261.79
MDL number:
PubChem Substance ID:

assay

97%

optical activity

[α]20/D −73.0°, c = 3 in ethanol

mp

261-263 °C (lit.)

SMILES string

Cl[H].C[C@H](N[C@@H](C)c1ccccc1)c2ccccc2

Application

The addition of lithium enolates to chiral 2-(aminomethyl)acrylates prepared from this C2-symmetrical amine results in the diastereoselective formation of β-amino acid esters. This amine has been employed as a chiral base in the synthesis of 3-substituted- and 3,3-disubstituted-γ-butyrolactones via enantioselective deprotonation of cyclobutane derivatives. It has also been used in a new method for the synthesis of β-aminophosphine derivatives of potential value as asymmetric ligands.

Certificate of Analysis

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Certificate of Origin

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Booth, B.L. et al.
Journal of the Chemical Society. Chemical Communications, 287-287 (1995)
Barnish, I.T. et al.
Tetrahedron Letters, 34, 1323-1323 (1993)
T. Honda et al.
Tetrahedron Asymmetry, 4, 1475-1475 (1993)

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