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

[1] MAGNESIUM AMIDE BASES AND AMIDO-GRIGNARDS .1. ORTHO-MAGNESIATION [J].

EATON, PE ;

LEE, CH ;

XIONG, YH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) :8016-8018

[2]

Henderson KW, 2001, CHEM-EUR J, V7, P3430, DOI 10.1002/1521-3765(20010817)7:16<3430::AID-CHEM3430>3.0.CO

[3]

2-1

[4] A CONVENIENT SYNTHESIS OF OPTICALLY PURE DIMETHYL 1,1'-BINAPHTHALENE-2,2'-DICARBOXYLATE FROM 1,1'-BINAPHTHALENE-2,2'-DIOL [J].

OHTA, T ;

ITO, M ;

INAGAKI, K ;

TAKAYA, H .

TETRAHEDRON LETTERS, 1993, 34 (10) :1615-1616

[5] Design of N-spiro C2-symmetric chiral quaternary ammonium bromides as novel chiral phase-transfer catalysts:: Synthesis and application to practical asymmetric synthesis of α-amino acids [J].

Ooi, T ;

Kameda, M ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (17) :5139-5151

[6] Asymmetric induction in the Neber rearrangement of simple ketoxime sulfonates under phase-transfer conditions: Experimental evidence for the participation of an anionic pathway [J].

Ooi, T ;

Takahashi, M ;

Doda, K ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (26) :7640-7641

[7]

Ooi T, 2002, ANGEW CHEM INT EDIT, V41, P1551, DOI 10.1002/1521-3773(20020503)41:9<1551::AID-ANIE1551>3.0.CO

[8]

2-L

[9]

Ooi T, 2001, SYNTHESIS-STUTTGART, P1716

[10] Practical catalytic enantioselective synthesis of α,α-dialkyl-α-amino acids by chiral phase-transfer catalysis [J].

Ooi, T ;

Takeuchi, M ;

Kameda, M ;

Maruoka, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (21) :5228-5229

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