The asymmetric catalytic aldol reaction of allenolates with aldehydes using N-fluoroacyl oxazaborolidine as the catalyst

被引：60

作者：

Li, GG ^{[1
]}

Wei, HX ^{[1
]}

Phelps, BS ^{[1
]}

Purkiss, DW ^{[1
]}

Kim, SH ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 06期

关键词：

D O I：

10.1021/ol000377+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The asymmetric catalytic aldol reaction of silyl allenolates with aldehydes has been achieved by using N-C3F7CO oxazaborolidine as the catalyst. The fluoroacyl group of the catalyst was found to be crucial for control of enantioselectivity. The reaction provides the first enantioselective approach to beta -halo Baylis-Hillman-type adducts.

引用

页码：823 / 826

页数：4

共 57 条

[41] Nelson SG, 2000, ANGEW CHEM INT EDIT, V39, P1323, DOI 10.1002/(SICI)1521-3773(20000403)39:7<1323::AID-ANIE1323>3.0.CO
[42] 2-X
[43] Catalyzed enantioselective aldol additions of latent enolate equivalents
Nelson, SG
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (03) : 357 - 389
[44] EFFICIENT OXIDATION OF PHENYL GROUPS TO CARBOXYLIC-ACIDS WITH RUTHENIUM TETRAOXIDE - A SIMPLE SYNTHESIS OF (R)-GAMMA-CAPROLACTONE, THE PHEROMONE OF TROGODERMA-GRANARIUM
NUNEZ, MT
MARTIN, VS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (06) : 1928 - 1932
[45] NEW CATALYSTS FOR THE ASYMMETRIC ALDOL REACTION - CHIRAL BORANES PREPARED FROM ALPHA,ALPHA-DISUBSTITUTED GLYCINE ARENESULFONAMIDES
PARMEE, ER
TEMPKIN, O
MASAMUNE, S
ABIKO, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9365 - 9366
[46] Ramachandran PV, 1999, CHEM COMMUN, P1979
[47] SARTOR D, 1990, SYNLETT, P197
[48] TAKASU M, 1990, SYNLETT, P194
[49] BETA-HALOVINYL KETONES - SYNTHESIS FROM ACETYLENIC KETONES
TANIGUCHI, M
KOBAYASHI, S
NAKAGAWA, M
HINO, T
KISHI, Y
[J]. TETRAHEDRON LETTERS, 1986, 27 (39) : 4763 - 4766
[50] ALDOL REACTION OF ALLENOLATES GENERATED VIA 1,4-ADDITION OF IODIDE ANION OR ITS EQUIVALENT TO ALPHA, BETA-ACETYLENIC KETONES
TANIGUCHI, M
HINO, T
KISHI, Y
[J]. TETRAHEDRON LETTERS, 1986, 27 (39) : 4767 - 4770

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