An alkylidene carbene C-H insertion strategy for the enantioselective synthesis of α,α-dialkyl-α-amino acids

被引：23

作者：

Gabaitsekgosi, R ^{[1
]}

Hayes, CJ ^{[1
]}

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 43期

关键词：

alkylidene carbene; enantioselective; alpha; alpha-dialkyl-alpha-amino acid; C-H insertion;

D O I：

10.1016/S0040-4039(99)01613-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of the alpha,alpha-dialkyl-alpha-amino acid (1S,3R)-2,5-methano-leucine has been achieved using an alkylidene carbene 1,5-C-H insertion reaction as a key step. Treatment of the ketone 11 with 1.2 equivalents of lithio(trimethylsilyl)diazomethane in THF resulted in the formation of the cyclopentene 13 in 62% yield. The enantiomeric excess of the product 18 was determined to be >95% by chiral HPLC (Chiracel OD column). (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7713 / 7716

页数：4

共 17 条

[1]

Campbell AD, 1998, SYNTHESIS-STUTTGART, P1707

[2] SYNTHESIS, RESOLUTION, AND ABSOLUTE-CONFIGURATION OF THE ISOMERS OF THE NEURONAL EXCITANT 1-AMINO-1,3-CYCLOPENTANEDICARBOXYLIC ACID [J].

CURRY, K ;

PEET, MJ ;

MAGNUSON, DSK ;

MCLENNAN, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (04) :864-867

[3] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[4]

DOYLE MP, 1995, SYNLETT, P1075

[5] INTRAMOLECULAR C-H INSERTIONS OF ALKYLIDENECARBENES .2. STEREOCHEMISTRY AND ISOTOPE EFFECTS [J].

GILBERT, JC ;

GIAMALVA, DH ;

BAZE, ME .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (14) :2557-2563

[6] Carbamate-directed hydroboration: Enantioselective synthesis of the excitatory amino acid 1-aminocyclopentane-1,3-dicarboxylic acid [J].

Hodgson, DM ;

Thompson, AJ ;

Wadman, S .

TETRAHEDRON LETTERS, 1998, 39 (20) :3357-3358

[7] TOTAL SYNTHESIS OF (-)-ALTEMICIDIN - A NOVEL EXPLOITATION OF THE POTIER-POLONOVSKI REARRANGEMENT [J].

KENDE, AS ;

LIU, K ;

BRANDS, KMJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (42) :10597-10598

[8]

Ma DW, 1997, TETRAHEDRON-ASYMMETR, V8, P825

[9] GENERATION OF ALKYLIDENECARBENES BY THE ALKENYLATION OF CARBONYL-COMPOUNDS WITH LITHIOTRIMETHYLSILYLDIAZOMETHANE [J].

OHIRA, S ;

OKAI, K ;

MORITANI, T .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (09) :721-722

[10] Cyclohexonone construction by intramolecular alkylidene C-H insertion: Synthesis of (+)-cassiol [J].

Taber, DF ;

Meagley, RP ;

Doren, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5723-5728

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