Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation

被引：102

作者：

Crimmins, MT ^{[1
]}

Emmitte, KA ^{[1
]}

Katz, JD ^{[1
]}

机构：

[1] Univ N Carolina, Venable & Kenan Labs Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 14期

关键词：

D O I：

10.1021/ol006091m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The diastereoselective alkylation of glycolate oxazolidinones has been demonstrated as a method for the enantioselective preparation of alpha-alkoxy carboxylic acid derivatives and selectively protected 1,2-diols, Various protecting groups on the glycolate hydroxyl and multiple substitution patterns on allylic iodides are tolerated in the alkylation, Yields for the alkylations are typically 70-85% with diastereoselectivities of >98:2.

引用

页码：2165 / 2167

页数：3

共 31 条

[1] 1,2-amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis
Ager, DJ
Prakash, I
Schaad, DR
[J]. CHEMICAL REVIEWS, 1996, 96 (02) : 835 - 875
[2] CHIRAL SYNTHESIS VIA ORGANOBORANES .24. B-ALLYLBIS(2-ISOCARANYL)BORANE AS A SUPERIOR REAGENT FOR THE ASYMMETRIC ALLYLBORATION OF ALDEHYDES
BROWN, HC
RANDAD, RS
BHAT, KS
ZAIDLEWICZ, M
RACHERLA, US
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) : 2389 - 2392
[3] Synthesis of a C(22)-C(34) halichondrin B precursor via ring opening double ring closing metathesis
Burke, SD
Quinn, KJ
Chen, VJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (24) : 8626 - 8627
[4] ENANTIOSELECTIVE SYNTHESIS OF 2-BENZYLOXY ALCOHOLS AND 1,2-DIOLS VIA ALKYLATION OF CHIRAL GLYCOLATE IMIDES - A CONVENIENT APPROACH TO OPTICALLY-ACTIVE GLYCEROL DERIVATIVES
CARDILLO, G
ORENA, M
ROMERO, M
SANDRI, S
[J]. TETRAHEDRON, 1989, 45 (05) : 1501 - 1508
[5] Synthetic studies toward potent cytotoxic agents amphidinolides G and H:: Synthesis of the entire C15-C26 moiety of the top half
Chakraborty, TK
Suresh, VR
[J]. TETRAHEDRON LETTERS, 1998, 39 (42) : 7775 - 7778
[6] En route to a plant scale synthesis of the promising antitumor agent 12,13-desoxyepothilene B
Chappell, MD
Stachel, SJ
Lee, CB
Danishefsky, SJ
[J]. ORGANIC LETTERS, 2000, 2 (11) : 1633 - 1636
[7] Coppola G. M., 1997, HYDROXY ACIDS ENANTI
[8] Total synthesis of (+)-laurencin: An asymmetric alkylation-ring-closing metathesis approach to medium ring ethers
Crimmins, MT
Emmitte, KA
[J]. ORGANIC LETTERS, 1999, 1 (12) : 2029 - 2032
[9] Crimmins MT, 2000, SYNTHESIS-STUTTGART, P899
[10] 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

← 1 2 3 4 →