HIGHLY CHEMOSELECTIVE REDUCTION OF N-BOC PROTECTED LACTAMS

被引：96

作者：

PEDREGAL, C ^{[1
]}

EZQUERRA, J ^{[1
]}

ESCRIBANO, A ^{[1
]}

CARRENO, MC ^{[1
]}

RUANO, JLG ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID,DEPT QUIM ORGAN,E-28049 MADRID,SPAIN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(00)73047-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Boc protected lactams can be reduced chemoselectively in the presence of other groups such as esters, nitriles, carbamates or double bonds by first reducing the amide carbonyl group into the corresponding hemiaminal using lithium triethylborohydride followed by further reduction of the hemiaminal intermediate with triethylsilane/Boron trifluoride etherate. This method preserves the chirality present in the substrate.

引用

页码：2053 / 2056

页数：4

共 21 条

[1] STEREOSELECTIVE SYNTHESIS OF STATIN ANALOGS
BERNARDI, A
MICHELI, F
POTENZA, D
SCOLASTICO, C
VILLA, R
[J]. TETRAHEDRON LETTERS, 1990, 31 (34) : 4949 - 4952
[2] LITHIUM TRIETHYLBOROHYDRIDE - EXCEPTIONALLY POWERFUL NUCLEOPHILE IN DISPLACEMENT REACTIONS WITH ORGANIC HALIDES
BROWN, HC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (05) : 1669 - 1671
[3] DAK JA, 1969, J ORG CHEM, V34, P2543
[4] SYNTHESIS OF (2S,3S)-[3-2H1]-PROLINE AND (2S,3R)-[2,3-2H2]-PROLINE
DIETERICH, P
YOUNG, DW
[J]. TETRAHEDRON LETTERS, 1993, 34 (34) : 5455 - 5458
[5] ALDOL REACTIONS OF PYROGLUTAMATES - CHIRAL SYNTHESIS OF 4-ALPHA(S)-(ARYLMETHYL)PYROGLUTAMATES AND 4-BETA(R)-(ARYLMETHYL)PYROGLUTAMATES
DIKSHIT, DK
PANDAY, SK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) : 1920 - 1924
[6] STEREOSELECTIVE REACTIONS OF LITHIUM ENOLATES DERIVED FROM N-BOC PROTECTED PYROGLUTAMIC ESTERS
EZQUERRA, J
PEDREGAL, C
RUBIO, A
YRURETAGOYENA, B
ESCRIBANO, A
SANCHEZFERRANDO, F
[J]. TETRAHEDRON, 1993, 49 (38) : 8665 - 8678
[7] INTRAMOLECULAR N-(ACYLOXY)IMINIUM ION ALKYNE CYCLOADDITIONS - A NEW ROUTE TO BICYCLIC ALPHA-AMINO KETONES
FISHER, MJ
OVERMAN, LE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) : 1447 - 1459
[8] A MILD 2-STEP METHOD FOR THE HYDROLYSIS METHANOLYSIS OF SECONDARY AMIDES AND LACTAMS
FLYNN, DL
ZELLE, RE
GRIECO, PA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (14) : 2424 - 2426
[9] ONE POT SYNTHESIS AND CONFORMATION OF N-TERT-BUTYLOXYCARBONYL, O-PHENACYL DERIVATIVES OF PROLINE AND OTHER SECONDARY AMINO-ACIDS
HONDRELIS, J
LONERGAN, G
VOLIOTIS, S
MATSOUKAS, J
[J]. TETRAHEDRON, 1990, 46 (02) : 565 - 576
[10] KONET MJ, 1968, J ORG CHEM, V33, P3637

← 1 2 3 →