Highly diastereoselective Michael addition reactions of butane-2,3-diacetal desymmetrized glycolic acid.: Preparation of α-hydroxy-γ-amino acid derivatives

被引：35

作者：

Dixon, DJ ^{[1
]}

Ley, SV ^{[1
]}

Rodríguez, F ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 23期

关键词：

D O I：

10.1021/ol016708f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The butane-2,3-diacetal (BDA) desymmetrized glycolic acid building block undergoes efficient and highly diastereoselective lithium enolate Michael additions to alpha,beta -unsaturated ketones, lactones, and nitro olefins. Subsequent deprotection of these Michael adducts gives a-hydroxy acids in very high yield. Hydrogenation of the nitro group in some of the adducts leads to gamma -lactams, which can be easily converted into alpha -hydroxy-gamma -amino acid derivatives.

引用

页码：3753 / 3755

页数：3

共 15 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] 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
[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] 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
[5] 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
Ley, SV
Dixon, DJ
Guy, RT
Palomero, MA
Polara, A
Rodríguez, F
Sheppard, TD
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (24) : 3618 - 3627
[6] Butane-2,3-diacetal-desymmetrized glycolic acid -: A new building block for the stereoselective synthesis of enantiopure α-hydroxy acids
Díez, E
Dixon, DJ
Ley, SV
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (15) : 2906 - 2909
[7] 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
[8] 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
[9] Highly diastereoselective Michael addition of α-hydroxy acid derivatives and enantioselective synthesis of (+)-crobarbatic acid
Jang, DP
Chang, JW
Uang, BJ
[J]. ORGANIC LETTERS, 2001, 3 (07) : 983 - 985
[10] Highly stereoselective Michael addition reactions of CamTHP*-desymmetrized glycinamide for the synthesis of functionally dense amino acid derivatives
Dixon, DJ
Horan, RAJ
Monck, NJT
Berg, P
[J]. ORGANIC LETTERS, 2004, 6 (24) : 4427 - 4429

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