Studies on the generation of enolate anions from butane-2,3-diacetal protected glycolic acid derivatives and subsequent highly diastereoselective coupling reactions with aldehydes and acid chlorides

被引：37

作者：

Ley, SV ^{[1
]}

Dixon, DJ ^{[1
]}

Guy, RT ^{[1
]}

Palomero, MA ^{[1
]}

Polara, A ^{[1
]}

Rodríguez, F ^{[1
]}

Sheppard, TD ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2004年 / 2卷 / 24期

关键词：

D O I：

10.1039/b412790k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Highly diastereoselective coupling reactions of enolates derived from butane-2,3-diacetal protected glycolic acids 1 and 2 and their alkylated derivatives with aldehydes are reported together with their efficient acid-catalysed deprotection to yield enantiopure anti-2,3-dihydroxyesters. A procedure to provide the corresponding syn-2,3-dihydroxyesters is also described in two cases, proceeding via an acylation reduction sequence. An usual double addition reaction of butane-2,3-diacetal protected glycolic acid to small aliphatic acid chlorides provides a synthetically useful, densely-functionalised lactone after acidic deprotection.

引用

页码：3618 / 3627

页数：10

共 8 条

[1] Highly diastereoselective ketone aldol reactions of butane-2,3-diacetal desymmetrised glycolic acid
Dixon, DJ
Guarna, A
Ley, SV
Polara, A
Rodríguez, F
[J]. SYNTHESIS-STUTTGART, 2002, (14): : 1973 - 1978
[2] Diastereoselective aldol reactions with butane-2,3-diacetal protected glyceraldehyde derivatives
Knudsen, KR
Stepan, AF
Michel, P
Ley, SV
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (08) : 1471 - 1473
[3] Michael, Michael-aldol and Michael-Michael reactions of enolate equivalents of butane-2,3-diacetal protected glycolic acid derivatives
Ley, SV
Dixon, DJ
Guy, RT
Rodríguez, F
Sheppard, TD
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (22) : 4095 - 4107
[4] Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid.: Preparation of α-hydroxy-γ-amino acid derivatives
Dixon, DJ
Ley, SV
Rodríguez, F
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3753 - 3755
[5] Highly diastereoselective lithium enolate aldol reactions of butane-2,3-diacetal desymmetrized glycolic acid and deprotection to enantiopure anti-2,3-dihydroxy esters
Dixon, DJ
Ley, SV
Polara, A
Sheppard, T
[J]. ORGANIC LETTERS, 2001, 3 (23) : 3749 - 3752
[6] Synthesis of a ceramide sphingolipid as a potential sex pheromone of the hair crab Erimacrus isenbeckii using butane-2,3-diacetal desymmetrised glycolic acid building blocks
Dixon, DJ
Ley, SV
Lohmann, S
Sheppard, TD
[J]. SYNLETT, 2005, (03) : 481 - 484
[7] Consecutive three- and four-component coupling reactions with anions generated from a butane diacetal desymmetrized glycolic acid derivative
Dixon, DJ
Ley, SV
Rodríguez, F
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (24) : 4763 - +
[8] Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxyacid and amide derivatives
Ley, SV
Diez, E
Dixon, DJ
Guy, RT
Michel, P
Nattrass, GL
Sheppard, TD
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (24) : 3608 - 3617

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