Magnesium bromide diethyl etherate mediated highly diastereoselective aldol reaction between an aldehyde and a silyl enol ether

被引：21

作者：

Fujisawa, H ^{[1
]}

Sasaki, Y ^{[1
]}

Mukaiyama, T ^{[1
]}

机构：

[1] Sci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjyuku Ku, Tokyo 1628601, Japan

来源：

CHEMISTRY LETTERS | 2001年 / 03期

关键词：

D O I：

10.1246/cl.2001.190

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

High yield and excellent diastereoselectivity in the formation of methyl (2R,3R,5R,6S)-2,6-dibenzyloxy-7-(t-butyldimethylsiloxy)-3-hydroxy-5-(4-methoxybenzyloxy)-4,4-dimethylheptanoate 3 and methyl (2R,3R,4S)-2,4-dibenzyloxy-3-hydroxypentanoate 7 are achieved by aldol reaction between (Z)-2-benzyloxy-1-methoxy-1-(trimethylsiloxy)ethene 1 and chiral alkoxy aldehydes using three equivalents of MgBr2. OEt2. The following mechanism of the above aldol reaction proposes that MgBr2. OEt2 activated both chiral alkoxy aldehydes and silyl enolate, that is, magnesiumu enolate, formed by transmetalation from silyl enolate and MgBr2. OEt2, reacted with MgBr2. OEt2-chelated alkoxy aldehydes via the six-membered cyclic transition state.

引用

页码：190 / 191

页数：2

共 18 条

[1] MGBR2-PROMOTED ADDITION OF HETEROSUBSTITUTED METHYLKETENE SILYL ACETALS TO ALKOXY ALDEHYDES - DIASTEREOSELECTIVE SYNTHESIS OF 3,4-SYN 2-METHYLENE AND 2-(ALKOXYMETHYL)-3-HYDROXY-4-ALKOXY ESTERS [J].

BERNARDI, A ;

CARDANI, S ;

COLOMBO, L ;

POLI, G ;

SCHIMPERNA, G ;

SCOLASTICO, C .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :888-891

[2] A new magnesium-catalyzed doubly diastereoselective anti-aldol reaction leads to a highly efficient process for the total synthesis of lactacystin in quantity [J].

Corey, EJ ;

Li, WD ;

Reichard, GA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (10) :2330-2336

[3] TOTAL SYNTHESIS OF THE IONOPHORE ANTIBIOTIC X-206 - STUDIES RELEVANT TO THE STEREOSELECTIVE SYNTHESIS OF THE C(17)-C(26) SYNTHON [J].

EVANS, DA ;

BENDER, SL .

TETRAHEDRON LETTERS, 1986, 27 (07) :799-802

[4] ACYCLIC STEREOSELECTION .36. SIMPLE DIASTEREOSELECTION IN THE LEWIS ACID MEDIATED REACTIONS OF ENOL SILANES WITH ALDEHYDES [J].

HEATHCOCK, CH ;

DAVIDSEN, SK ;

HUG, KT ;

FLIPPIN, LA .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (15) :3027-3037

[5] TOTAL SYNTHESIS OF THE IMMUNOSUPPRESSANT (-)-FK-506 [J].

JONES, TK ;

MILLS, SG ;

REAMER, RA ;

ASKIN, D ;

DESMOND, R ;

VOLANTE, RP ;

SHINKAI, I .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :1157-1159

[6] REACTIVE ENOLATES FROM ENOL SILYL ETHERS [J].

KUWAJIMA, I ;

NAKAMURA, E .

ACCOUNTS OF CHEMICAL RESEARCH, 1985, 18 (06) :181-187

[7] TRANSITION STRUCTURES FOR THE ALDOL REACTIONS OF ANIONIC, LITHIUM, AND BORON ENOLATES [J].

LI, Y ;

PADDONROW, MN ;

HOUK, KN .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) :481-493

[8] Silylacetic esters: Enolate reactions and polyol preparation [J].

Mader, MM ;

Edel, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08) :2761-2764

[9] FACILE SYNTHESIS OF OPTICALLY-ACTIVE ANTI-ALPHA,BETA-DIHYDROXY ESTER DERIVATIVES [J].

MUKAIYAMA, T ;

UCHIRO, H ;

SHIINA, I ;

KOBAYASHI, S .

CHEMISTRY LETTERS, 1990, (06) :1019-1022

[10]

MUKAIYAMA T, 1990, CHEM LETT, P1901

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