Glycolate aldol reactions with boron enolates of bis-4-methoxyphenyl dioxanone

被引：22

作者：

Andrus, MB ^{[1
]}

Mendenhall, KG ^{[1
]}

Meredith, EL ^{[1
]}

Sekhar, BBVS ^{[1
]}

机构：

[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 10期

关键词：

aldol reaction; glycolate; enolate; diols; diasteroselection;

D O I：

10.1016/S0040-4039(02)00152-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The boron enolate of 5S,6S-bis-5,6-(4-methoxyphenyl)-2-dioxanone reacted with various aldehydes to produce anti glycolate aldol products in high yield with good selectivity. The outcome is consistent with an E-enolate reacting through a closed transition state. The adducts were protected and the auxiliary was conveniently removed with ceric ammonium nitrate to give useful intermediates. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1789 / 1792

页数：4

共 33 条

[1] Synthesis of the left-hand portion of geldanamycin using an anti glycolate aldol reaction
Andrus, MB
Meredith, EL
Sekhar, BBVS
[J]. ORGANIC LETTERS, 2001, 3 (02) : 259 - 262
[2] Highly selective syn glycolate aldol reactions with boron enolates of Masamune norephedrine esters
Andrus, MB
Sekhar, BBVS
Turner, TM
Meredith, EL
[J]. TETRAHEDRON LETTERS, 2001, 42 (41) : 7197 - 7201
[3] STRUCTURE-BASED DESIGN OF AN ACYCLIC LIGAND THAT BRIDGES FKBP12 AND CALCINEURIN
ANDRUS, MB
SCHREIBER, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) : 10420 - 10421
[4] Anti-selective glycolate aldol additions with an oxapyrone boron enolate
Andrus, MB
Sekhar, BBVS
Meredith, EL
Dalley, NK
[J]. ORGANIC LETTERS, 2000, 2 (19) : 3035 - 3037
[5] Total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and 2-deoxy-β-KDO
Burke, SD
Sametz, GM
[J]. ORGANIC LETTERS, 1999, 1 (01) : 71 - 74
[6] Cameron J. C., 1997, ORG REACTIONS, V51, P1
[7] Diastereoselective addition of prochiral metallo enolates to chiral 1-acylpyridinium salts
Comins, DL
Kuethe, JT
Hong, H
Lakner, FJ
Concolino, TE
Rheingold, AL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) : 2651 - 2652
[8] An asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of oxygen heterocycles: An efficient approach to the enantioselective synthesis of (+)-laurencin
Crimmins, MT
Choy, AL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) : 5653 - 5660
[9] Asymmetric aldol-ring-closing metathesis strategy for the enantioselective construction of six- to nine-membered oxygen heterocycles
Crimmins, MT
Choy, AL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) : 7548 - 7549
[10] ENAMTIOMERIC PURITY OF PHENYLETHYLENE GLYCOLE AND RELIABILITY OF PHENYLGLYOXYLATE ASYMMETRIC REDUCTIONS IN CONFIGURATIONAL ASSIGNMENTS
DALE, JA
MOSHER, HS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (11) : 4002 - &

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