Erythrulose as a multifunctional chiron: Highly stereoselective boron aldol additions

被引：17

作者：

Marco, JA ^{[1
]}

Carda, M

Falomir, E

Palomo, C

Oiarbide, M

Ortiz, JA

Linden, A

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

[2] Univ Jaume 1, Dept Quim Inorgan & Organ, E-12080 Castellon de La Plana, Spain

[3] Univ Basque Country, Fac Quim, Dept Quim Organ, E-20080 San Sebastian, Spain

[4] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(99)80113-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have investigated the formation of various metal enolates of 1-O-silylated erythrulose 3,4-acetonides. We were able to prepare boron enolates using Brown's dicyclohexylboron chloride/tertiary amine system. When these enolates were allowed to react with a range of achiral aldehydes, highly stereoselective aldol additions took place with formation of the syn/syn stereoisomer. This has been attributed to the exclusive formation of a Z boron enolate, which is in a sharp contrast with the usual behaviour of the aforementioned reagent. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：1065 / 1068

页数：4

共 53 条

[1] DIASTEREOSELECTIVE SYNTHESIS OF ANTI AND SYN ALPHA,BETA-DIHYDROXY THIOESTERS BY TITANIUM ENOLATE ALDOL CONDENSATION
ANNUNZIATA, R
CINQUINI, M
COZZI, F
BORGIA, AL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) : 6339 - 6342
[2] [Anonymous], 1984, ASYMMETRIC SYNTHESIS
[3] BEAU JM, 1990, RECENT PROGRESS IN THE CHEMICAL SYNTHESIS OF ANTIBIOTICS, P135
[4] ORIGINS OF STEREOSELECTIVITY IN CHIRAL BORON ENOLATE ALDOL REACTIONS - A COMPUTATIONAL STUDY USING TRANSITION-STATE MODELING
BERNARDI, A
CAPELLI, AM
COMOTTI, A
GENNARI, C
GARDNER, M
GOODMAN, JM
PATERSON, I
[J]. TETRAHEDRON, 1991, 47 (20-21) : 3471 - 3484
[5] BLIZZARD T, 1990, RECENT PROGRESS IN THE CHEMICAL SYNTHESIS OF ANTIBIOTICS, P65
[6] BRAUN M, 1996, HOUBENWEYLS METHODS, V3, P1603
[7] ENOLBORATION .2. DICYCLOHEXYLCHLOROBORANE TRIETHYLAMINE AS A CONVENIENT REAGENT FOR REGIOSELECTIVE AND STEREOSELECTIVE ENOLBORATION OF REPRESENTATIVE CLASSES OF KETONES
BROWN, HC
DHAR, RK
GANESAN, K
SINGARAM, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) : 2716 - 2721
[8] MAJOR EFFECT OF THE LEAVING GROUP IN DIALKYLBORON CHLORIDES AND TRIFLATES IN CONTROLLING THE STEREOSPECIFIC CONVERSION OF KETONES INTO EITHER (E)-ENOL OR (Z)-ENOL BORINATES
BROWN, HC
DHAR, RK
BAKSHI, RK
PANDIARAJAN, PK
SINGARAM, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) : 3441 - 3442
[9] ENOLBORATION .4. AN EXAMINATION OF THE EFFECT OF THE LEAVING GROUP-(X) ON THE STEREOSELECTIVE ENOLBORATION OF KETONES WITH VARIOUS R2BX/ET3N - NEW REAGENTS FOR THE SELECTIVE GENERATION OF EITHER Z-ENOL OR E-ENOL BORINATES FROM REPRESENTATIVE KETONES
BROWN, HC
GANESAN, K
DHAR, RK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (01) : 147 - 153
[10] ENOLBORATION .3. AN EXAMINATION OF THE EFFECT OF VARIABLE STERIC REQUIREMENTS OF R ON THE STEREOSELECTIVE ENOLBORATION OF KETONES WITH R2BCL/ET3N - BIS(BICYCLO[2.2.2]OCTYL)CHLOROBORANE TRIETHYLAMINE, A NEW REAGENT WHICH ACHIEVES THE SELECTIVE GENERATION OF E-ENOLBORINATES FROM REPRESENTATIVE KETONES
BROWN, HC
GANESAN, K
DHAR, RK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) : 3767 - 3772

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