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2001
diastereoselective syntheses, enantioselective syntheses
diastereoselective syntheses, enantioselective syntheses (incl. cis/trans-isomerism)
O 0031
Asymmetric Synthesis of Homoallylic Amines and Functionalized
16 - 033 Pyrrolidines via Direct Amino-Crotylation of in situ Generated
Imines.
— Lewis acid promoted condensation of chiral (E)-crotylsilanes
(III), (V) and (VIII) with in situ generated N-acyl imines or sulfonyl imines
represents a novel access to homoallylic amines [cf. (IV) or (XII)] and
silyl-functionalized pyrrolidines (IX) and (X). Homoallylic amines are formed
in moderate to excellent syn-diastereoselectivity. For aryl N-acyl imines,
the reaction pathway strongly depends on the reaction temperature. While
at higher temperatures homoallylic amines [cf. (IVa)] are formed, at low
temperatures functionalized pyrrolidines [cf. (IX)] are obtained. In double
stereodifferentiating reactions [(XI)→(XII)], good levels of syn-selectivity for
the newly formed stereocenters are obtained. — (SCHAUS, JENNIFER V.;
JAIN, NARESHKUMAR; PANEK, JAMES S.; Tetrahedron 56 (2000) 52,
10263-10274; Dep. Chem., Boston Univ., Boston, MA 02215, USA; EN)
1
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