First example of a total axial to centered chirality transfer in the [2+2+2] cycloadditions of allenediynes

被引:0
作者
Buisine, O [1 ]
Aubert, C [1 ]
Malacria, M [1 ]
机构
[1] Univ Paris 06, CNRS, Lab Chim Organ Synth, F-75252 Paris, France
来源
SYNTHESIS-STUTTGART | 2000年 / 07期
关键词
alkynes; allenes; chirality; cycloadditions; cobalt;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cobalt-mediated [2+2+2] cycloaddition of allene-diynes bearing a phosphine oxide group at one alkyne terminus is a completely regio-, chemo- and diastereoselective high yielding process. Moreover. a total transfer of chiral information from axial to centered chirality is evident, which makes this reaction a new and powerful tool for the preparation of enantiomerically enriched tricyclic derivatives.
引用
收藏
页码:985 / 989
页数:5
相关论文
共 35 条
[1]   Pauson-Khand reaction with allenic compounds .2. Reactivity of functionalized allenes. [J].
Ahmar, M ;
Chabanis, O ;
Gauthier, J ;
Cazes, B .
TETRAHEDRON LETTERS, 1997, 38 (30) :5277-5280
[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]   ALLENES AS NEW PARTNERS IN INTRAMOLECULAR COBALT-MEDIATED [2+2+2] CYCLOADDITION REACTIONS [J].
AUBERT, C ;
LLERENA, D ;
MALACRIA, M .
TETRAHEDRON LETTERS, 1994, 35 (15) :2341-2344
[4]   CHEMISTRY OF ALLENE .2. REACTION OF ALLENE WITH ACETYLENES [J].
BENSON, RE ;
LINDSEY, RV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (16) :4250-4253
[5]   ETA-3-BONDING OF PHENYLALLENYL IN A ZIRCONOCENE COMPLEX [J].
BLOSSER, PW ;
GALLUCCI, JC ;
WOJCICKI, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :2994-2995
[6]  
BOWDE FL, 1976, COORDIN CHEM REV, V26, P81
[7]   An intramolecular allenic [2+2+1]cycloaddition [J].
Brummond, KM ;
Wan, HH ;
Kent, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (19) :6535-6545
[8]   CARBOPALLADATION OF FUNCTIONALIZED ALLENES - REGIOSELECTIVITY OF THE REACTION OF CARBONUCLEOPHILES WITH THE INTERMEDIATE PI-ALLYL PALLADIUM COMPLEXES [J].
CHAPTAL, N ;
COLOVRAYGOTTELAND, V ;
GRANDJEAN, C ;
CAZES, B ;
GORE, J .
TETRAHEDRON LETTERS, 1991, 32 (15) :1795-1798
[9]   Novel Pd(0)-catalyzed intramolecular reactions of allylic acetates with allenic moieties followed by tandem cyclization [J].
Doi, T ;
Yanagisawa, A ;
Nakanishi, S ;
Yamamoto, K ;
Takahashi, T .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (08) :2602-2603
[10]   SYNTHESIS AND STEREOCHEMISTRY OF ALLENES .2. ABSOLUTE-CONFIGURATIONS OF 1-HALOGENO-3,4,4-TRIMETHYLPENTA-1,2-DIENES AND 3,4,4-TRIMETHYLPENT-1-YN-3-OL [J].
ELSEVIER, CJ ;
MOOIWEER, HH .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (08) :1536-1539