Scope and limitations of the alkylidene carbene 1,5-CH insertion reactions of α-amino acid-derived substrates

被引:8
作者
Mapitse, R [1 ]
Hayes, CJ [1 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
关键词
D O I
10.1016/S0040-4039(02)00585-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A range of alpha-amino acid-derived cyclisation precursors were synthesised from suitably protected alpha-amino esters, via a Dibal-H/Wittig/catalytic hydrogenation strategy and each of these was subjected to alkylidene carbene-forming conditions (lithio(trimethylsilyl)diazomethane, THF). The cyclisations proceeded in poor to good yield, with the best cyclisations occurring to produce spirocyclic products. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:3541 / 3542
页数:2
相关论文
共 13 条
[1]  
Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
[2]  
2-V
[3]   ASYMMETRIC CREATION OF QUATERNARY CARBON CENTERS [J].
FUJI, K .
CHEMICAL REVIEWS, 1993, 93 (06) :2037-2066
[4]   An alkylidene carbene C-H insertion strategy for the enantioselective synthesis of α,α-dialkyl-α-amino acids [J].
Gabaitsekgosi, R ;
Hayes, CJ .
TETRAHEDRON LETTERS, 1999, 40 (43) :7713-7716
[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]   A convenient method for 3-pyrroline synthesis [J].
Green, MP ;
Prodger, JC ;
Sherlock, AE ;
Hayes, CJ .
ORGANIC LETTERS, 2001, 3 (21) :3377-3379
[7]  
MCKILLOP A, 1994, SYNTHESIS, V31
[8]   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
[9]   C-H INSERTION METHOD FOR THE CHIRAL TERTIARY ALCOHOL - FORMAL SYNTHESIS OF (-)-FRONTALIN [J].
OHIRA, S ;
ISHI, S ;
SHINOHARA, K ;
NOZAKI, H .
TETRAHEDRON LETTERS, 1990, 31 (07) :1039-1040
[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