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2005
Polyphenylalkane derivatives
Q 0720
Asymmetric Synthesis of Diarylmethyl Amines by Rhodium-Catalyzed AsymmetAddition of Aryl Titanium Reagents to Imines. — The asymmetric synthesis of
11- 109 ric
diarylmethylamines is smoothly achieved by addition of aryl titanium reagents (II) and
(V) to N-benzylidene sulfonamides (I) and (IV), resp., using a rhodium—axially chiral
diphosphine complex. The highest enantioselectivities (up to 98% e.e.) are achieved
with the SEGPHOS ligand and with bulky sulfonamides like triisopropylphenylsulfonamides. In most cases, the removal of the sulfonyl group is achieved using standard
techniques (Li—liq. NH3). Better results in the presence of reducible groups, however,
are achieved with alternative strategies, e.g. SmI2—HMPA or RedAl. —
(HAYASHI*, T.; KAWAI, M.; TOKUNAGA, N.; Angew. Chem., Int. Ed. 43 (2004)
45, 6125-6128; Dep. Chem., Grad. Sch. Sci., Kyoto Univ., Sakyo, Kyoto 606, Japan;
Eng.) — Mischke
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