F3B•OEt2-promoted intramolecular Si to C phenyl group migration:: A highly diastereoselective synthesis of (4S,5S)-4-hydroxy-5-phenyl-2-pyrrolidinone

被引：1

作者：

Liu, LX

Huang, PQ ^{[1
]}

机构：

[1] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem, Fujian 361005, Peoples R China

[2] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Province, Fujian 361005, Peoples R China

[3] Ganan Teachers Coll, Dept Chem & Biol, Jiangxi, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2006年 / 36卷 / 08期

关键词：

boron trifluoride etherate; N-acyliminium; phenyl migration; 2-pyrrolidinone;

D O I：

10.1080/00397910500503538

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly diastereoselective approach to N-protected cis-(4S,5S)-4-hydroxy-5-phenyl-2-pyrrolidinone is reported. The key step is a boron trifluoride etherate-promoted chemoselective intramolecular Si -> C phenyl group migration.

引用

页码：1131 / 1139

页数：9

共 50 条

[1] An improved synthesis of (4S,5S)-2-Phenyl-4-(methoxycarbonyl)-5-isopropyloxazoline from (S)-phenylglycinol
Panek, JS
Masse, CE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07): : 2382 - 2384
[2] (4S,5S)-4-METHYL-5-PHENYL-1,3-OXAZOLIDIN-2-ONE
ROBINSON, PD
HUA, DH
GOOD, LA
WANG, H
MEYERS, CY
[J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1993, 49 : 1238 - 1240
[3] AN IMPROVED SYNTHESIS OF (4S,5S)-2,2-DIMETHYL-4-PHENYL-1,3-DIOXAN-5-AMINE
NORDIN, IC
THOMAS, JA
[J]. TETRAHEDRON LETTERS, 1984, 25 (50) : 5723 - 5724
[4] (4S)-2-phenyl-4-tert-butylaminomethyl-1,3-dioxolanes as side products of (5S)-2-phenyl-3-tert-butyl-5-hydroxymethyloxazolidine preparation
Bredikhin, AA
Novikova, VG
Bredikhina, ZA
[J]. ZHURNAL ORGANICHESKOI KHIMII, 1997, 33 (03): : 427 - 429
[5] (+)-(4R,5S)-4-methyl-5-phenyl-3-[2(S)-phenyl-propionyl]oxazolidin-2-one
Coumbarides, Gregory S.
Eames, Jason
Motevalli, Majid
Malatesti, Nela
Yohannes, Yonas
[J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O4032 - O4034
[6] (3R,4S,5S)-5-BENZYL-4-HYDROXY-3-[1(S)-(1,1-DIMETHYLETHOXYCARBONYLAMINO)-2-PHENYL-ETHYL]PYRROLIDIN-2-ONE
WEBER, HP
ETTMAYER, P
HUBNER, M
GSTACH, H
[J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1995, 51 : 2139 - 2141
[7] An improved synthesis of (4S,5S)-2-phenyl-4-methoxycarbonyl-5-isopropyloxazoline from (S)-phenylglycinol (vol 63, pg 2382, 1998)
Panek, JS
Masse, CE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (15): : 5294 - 5294
[8] Synthesis of (2S,4S,5S)-5-hydroxy-4-methylpipecolic acid via amide methylenation of 5-hydroxy-4-methyl-2-piperidinone with dimethyltitanocene
Herdeis, C
Heller, E
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (07) : 1115 - 1121
[9] SYNTHESIS OF (2R,4S,5S)-EPIALLOMUSCARINE, (2S,3R,5S)-ISOEPIALLOMUSCARINE, AND (2S,3S,4S,5S)-3-HYDROXYEPIALLOMUSCARINE FROM ALPHA-D-GLUCOSE
WANG, PC
JOULLIE, MM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (26): : 5359 - 5363
[10] (2S*,4S*,5R*)-4-methyl-2-[(5S*)-3-methyl-4,5-dihydroisoxazol-5-yl]-5-phenyl-3(toluene-4-sulfonyl) oxazolidine
Rochon, FD
Breau, L
[J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1999, 55 : 1373 - 1375

← 1 2 3 4 5 →