The first regioselective α-deprotonation and functionalization of allenamides.: An application in intramolecular Pauson-Khand-type cycloadditions

被引:64
作者
Xiong, H [1 ]
Hsung, RP [1 ]
Wei, LL [1 ]
Berry, CR [1 ]
Mulder, JA [1 ]
Stockwell, B [1 ]
机构
[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA
关键词
D O I
10.1021/ol000181+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first regioselective alpha-deprotonation and functionalization of electron-deficient allenamines are described here. The acidities of alpha- and gamma-allenic protons of these allenamides are readily differentiated using strong bases, thereby allowing regioselective substitutions at either the alpha- or gamma-allenic position, A specific synthetic application of the novel alpha-substituted allenamides in intramolecular Pauson-Khand-type cycloadditions is also described here.
引用
收藏
页码:2869 / 2871
页数:3
相关论文
共 33 条
[1]   PAUSON-KHAND REACTION WITH ALLENIC COMPOUNDS .1. SYNTHESIS OF 4-ALKYLIDENE-2-CYCLOPENTENONES [J].
AHMAR, M ;
ANTRAS, F ;
CAZES, B .
TETRAHEDRON LETTERS, 1995, 36 (25) :4417-4420
[2]   Pauson-Khand cycloaddition of alpha,omega-allenynes. [J].
Ahmar, M ;
Locatelli, C ;
Colombier, D ;
Cazes, B .
TETRAHEDRON LETTERS, 1997, 38 (30) :5281-5284
[3]   Thermal promotion of the cobalt catalyzed intramolecular Pauson-Khand reaction - An alternative experimental protocol for cyclopentenone synthesis [J].
Belanger, DB ;
O'Mahony, DJR ;
Livinghouse, T .
TETRAHEDRON LETTERS, 1998, 39 (42) :7637-7640
[4]   Hexacarbonyldicobalt-alkyne complexes as convenient Co2(CO)8 surrogates in the catalytic Pauson-Khand reaction [J].
Belanger, DB ;
Livinghouse, T .
TETRAHEDRON LETTERS, 1998, 39 (42) :7641-7644
[5]   Recent advances in the Pauson-Khand reaction and related [2+2+1] cycloadditions [J].
Brummond, KM ;
Kent, JL .
TETRAHEDRON, 2000, 56 (21) :3263-3283
[6]   An intramolecular allenic [2+2+1]cycloaddition [J].
Brummond, KM ;
Wan, HH ;
Kent, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6535-6545
[7]   The allenic Pauson-Khand cycloaddition.: Dependence in π-bond selectivity on substrate structure. [J].
Brummond, KM ;
Wan, H .
TETRAHEDRON LETTERS, 1998, 39 (09) :931-934
[8]  
CORBEL B, 1976, TETRAHEDRON LETT, P835
[9]  
CRAIG JC, 1980, TETRAHEDRON LETT, V21, P2587
[10]   A NEW STRATEGY FOR THE CONVERSION OF PENAMS INTO CEPHEMS VIA ALLENE CHEMISTRY .1. [J].
FARINA, V ;
KANT, J .
TETRAHEDRON LETTERS, 1992, 33 (25) :3559-3562