Boron-mediated stereoselective syntheses of γ,γ-disubstituted allenamides

被引:19
作者
Hyland, CJT [1 ]
Hegedus, LS [1 ]
机构
[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA
关键词
D O I
10.1021/jo051385c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] Propargylic boranes generated by lithiation of optically active N-propargyloxazolidinones undergo reaction with a range of aldehydes to produce gamma,gamma-disubstituted allenamides with good diastereoselectivity.
引用
收藏
页码:8628 / 8630
页数:3
相关论文
共 19 条
[1]   Nucleophilic transition metal based cyclization of allenes [J].
Bates, RW ;
Satcharoen, V .
CHEMICAL SOCIETY REVIEWS, 2002, 31 (01) :12-21
[2]   Rhodium(I)-catalyzed ene-allene carbocyclization strategy for the formation of azepines and oxepines [J].
Brummond, KM ;
Chen, HF ;
Mitasev, B ;
Casarez, AD .
ORGANIC LETTERS, 2004, 6 (13) :2161-2163
[3]  
FARINA V, 1996, TETRAHEDRON LETT, V33, P3559
[4]  
Gaul C, 2002, HELV CHIM ACTA, V85, P963, DOI 10.1002/1522-2675(200204)85:4<963::AID-HLCA963>3.0.CO
[5]  
2-6
[6]   HIGHLY REGIODIASTEREOSELECTIVE AND SYN-DIASTEREOSELECTIVE SYNTHESIS OF 4-HYDROXY-1,2-ALKADIENYLCARBAMATES FROM ALPHA-TITANATED 2-ALKYNYLCARBAMATES AND ALDEHYDES [J].
HOPPE, D ;
GONSCHORREK, C ;
SCHMIDT, D ;
EGERT, E .
TETRAHEDRON, 1987, 43 (11) :2457-2466
[7]   Transition metal-catalyzed/mediated reaction of allenes with a nucleophilic functionality connected to the α-carbon atom [J].
Ma, SM .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (09) :701-712
[8]   Synthesis of a C1-C21 subunit of the protein phosphatase inhibitor tautomycin: A formal total synthesis [J].
Marshall, JA ;
Yanik, MM .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1373-1379
[9]   SYNTHESIS OF TRIMETHYLSILYL-SUBSTITUTED ALPHA-ALLENIC AND BETA-ACETYLENIC AMINES FROM IMINES AND PROPARGYLIC AND ALLENIC ORGANOBORANES [J].
NIKAM, SS ;
WANG, KK .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (12) :2193-2195
[10]  
Rameshkumar C, 2003, SYNLETT, P1241