Parallel kinetic resolution of 4-alkynals catalyzed by Rh(I)/Tol-BINAP: Synthesis of enantioenriched cyclobutanones and cyclopentenones

被引:135
作者
Tanaka, K [1 ]
Fu, GC [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
关键词
D O I
10.1021/ja035489l
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Rh(I)/(R)-Tol-BINAP catalyst reacts with a racemic mixture of 4-alkynals to selectively furnish a cyclobutanone from the (R)-substrate and a cyclopentenone from the (S)-substrate. This method is noteworthy from several standpoints, including the scarcity of parallel kinetic resolutions (especially those that are catalyzed or that involve carbon-carbon bond formation) and the dearth of catalytic processes that generate enantioenriched cyclobutanones. Copyright © 2003 American Chemical Society.
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页码:8078 / 8079
页数:2
相关论文
共 19 条
[1]   Parallel kinetic resolution of racemic mixtures: a new strategy for the preparation of enantiopure compounds? [J].
Dehli, JR ;
Gotor, V .
CHEMICAL SOCIETY REVIEWS, 2002, 31 (06) :365-370
[2]  
Eames J, 2000, ANGEW CHEM INT EDIT, V39, P885, DOI 10.1002/(SICI)1521-3773(20000303)39:5<885::AID-ANIE885>3.0.CO
[3]  
2-2
[4]   ASYMMETRIC ALLYLIC ALKYLATION OF 1,3-DISUBSTITUTED 2-PROPENYL ACETATES CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-PALLADIUM COMPLEX [J].
HAYASHI, T ;
YAMAMOTO, A ;
ITO, Y .
CHEMISTRY LETTERS, 1987, (01) :177-180
[5]   1,2-ASYMMETRIC REARRANGEMENTS IN CHIRAL SULFINYLCYCLOPROPANE SYSTEMS - ASYMMETRIC-SYNTHESIS OF ALPHA,ALPHA-DISUBSTITUTED CYCLOBUTANONES [J].
HIROI, K ;
NAKAMURA, H ;
ANZAI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1249-1250
[6]   MODELS FOR ASYMMETRIC [2+2] CYCLO-ADDITIONS [J].
HOUGE, C ;
FRISQUEHESBAIN, AM ;
MOCKEL, A ;
GHOSEZ, L ;
DECLERCQ, JP ;
GERMAIN, G ;
VANMEERSSCHE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (10) :2920-2921
[7]  
Hoveyda AH, 1998, CURR ORG CHEM, V2, P489
[8]   Rearrangement of 1-(1-alkynyl)cyclopropanols to 2-cyclopentenones via their hexacarbonyldicobalt complexes.: A new use of alkyne-Co2(CO)6 complexes in organic synthesis [J].
Iwasawa, N ;
Matsuo, T ;
Iwamoto, M ;
Ikeno, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :3903-3914
[9]  
Kagan H.B., 2007, TOPICS STEREOCHEMIST, V18, P249, DOI 10.1002/9780470147276.ch4
[10]  
Keith JM, 2001, ADV SYNTH CATAL, V343, P5, DOI 10.1002/1615-4169(20010129)343:1<5::AID-ADSC5>3.0.CO