New, improved procedure for the synthesis of structurally diverse N-spiro C2-symmetric chiral quaternary ammonium bromides

被引：65

作者：

Ooi, T ^{[1
]}

Uematsu, Y ^{[1
]}

Maruoka, K ^{[1
]}

机构：

[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Sakyo Ku, Kyoto 6068502, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 11期

关键词：

D O I：

10.1021/jo030032f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Selective, direct ortho magnesiation of (S)-2,2'-bis(isopropoxycarbonyl)-1,1'-binaphthyl (6) has been achieved under mild conditions, using magnesium bis(2,2,6,6-tetra-methylpiperamide) [Mg(TMP)(2)]. In combination with the subsequent reaction with the appropriate electrophiles, bromine and iodine, this method constitutes a key step in establishing a new and concise synthetic route to a wide variety of N-spiro C-2-symmetric chiral quaternary ammonium bromides of type 1.

引用

页码：4576 / 4578

页数：3

共 14 条

[11] Molecular design of a C2-symmetric chiral phase-transfer catalyst for practical asymmetric synthesis of α-amino acids [J].

Ooi, T ;

Kameda, M ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (27) :6519-6520

[12] Facile synthesis of L-Dopa tert-butyl cater by catalytic enantioselective phase-transfer alkylation [J].

Ooi, T ;

Kameda, M ;

Tannai, H ;

Maruoka, K .

TETRAHEDRON LETTERS, 2000, 41 (43) :8339-8342

[13]

Seki M, 2000, SYNTHESIS-STUTTGART, P1677

[14] Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995-1998 [J].

Suzuki, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :147-168

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