Phase-transfer-catalyzed asymmetric glycolate alkylation

被引：29

作者：

Andrus, MB ^{[1
]}

Hicken, EJ ^{[1
]}

Stephens, JC ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 13期

关键词：

D O I：

10.1021/ol0491235

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Asymmetric surrogate glycolate alkylation has been performed under phase-transfer conditions. Diphenylmethyloxy-2,5-dimethoxyacetophenone with trifluorobenzyl cinchonidinium catalyst and cesium hydroxide provided alkylation products at -35 degreesC in high yield (80-99%) and with excellent enantioselectivities (90:10 to 95:5). Useful a-hydroxy products were obtained using bis-TMS peroxide Baeyer-Villiger conditions and selective transesterification. The intermediate aryl ester can be obtained with >99% ee after a single recrystallization. A tight ion-pair model for the observed (S)-stereoinduction is proposed.

引用

页码：2289 / 2292

页数：4

共 17 条

[1] Highly enantioselective phase transfer catalyzed alkylation of a 3-oxygenated propionic ester equivalent; applications and mechanism
Corey, EJ
Bo, YX
Busch-Petersen, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) : 13000 - 13001
[2] A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions
Corey, EJ
Xu, F
Noe, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12414 - 12415
[3] Diastereoselective alkylations of oxazolidinone glycolates: A useful extension of the Evans asymmetric alkylation
Crimmins, MT
Emmitte, KA
Katz, JD
[J]. ORGANIC LETTERS, 2000, 2 (14) : 2165 - 2167
[4] ASYMMETRIC OXIDATION OF ESTER AND AMIDE ENOLATES USING NEW (CAMPHORYLSULFONYL)OXAZIRIDINES
DAVIS, FA
HAQUE, MS
ULATOWSKI, TG
TOWSON, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (12) : 2402 - 2404
[5] Gottlich R, 1997, SYNLETT, P971
[6] An unusual electronic effect of an aromatic-F in phase-transfer catalysts derived from Cinchona-alkaloid
Jew, SS
Yoo, MS
Jeong, BS
Park, IY
Park, HG
[J]. ORGANIC LETTERS, 2002, 4 (24) : 4245 - 4248
[7] Kacprzak K, 2001, SYNTHESIS-STUTTGART, P961
[8] LOWRY TH, 1981, MECH THEORY ORGANIC, P651
[9] A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids - Application in the enantioselective synthesis of alpha-amino acids
Lygo, B
Wainwright, PG
[J]. TETRAHEDRON LETTERS, 1997, 38 (49) : 8595 - 8598
[10] Enantioselective amino acid synthesis by chiral phase-transfer catalysis
Maruoka, K
Ooi, T
[J]. CHEMICAL REVIEWS, 2003, 103 (08) : 3013 - 3028

← 1 2 →