A CONCISE ENANTIOSELECTIVE SYNTHESIS OF ALLYLAMINES AND N-BOC-BETA-AMINO ACIDS

被引：40

作者：

ALCON, M ^{[1
]}

CANAS, M ^{[1
]}

POCH, M ^{[1
]}

MOYANO, A ^{[1
]}

PERICAS, MA ^{[1
]}

RIERA, A ^{[1
]}

机构：

[1] UNIV BARCELONA,DEPT QUIM ORGAN,E-08028 BARCELONA,SPAIN

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(00)76766-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new and efficient enantioseledive synthesis of allylamines and N-Boc-beta-amino acids has been developed. Starting from enantiomerically enriched N-diphenylmethyl-3-amino-1,2-diols, allylamines are easily obtained by a Corey-Hopkins deoxygenative protocol. After a change in the nitrogen protecting group, the resulting N-Boc allylamines are converted into beta-amino acids by hydroboration with 9-BBN followed by oxidation with PDC in DMF.

引用

页码：1589 / 1592

页数：4

共 46 条

[1] STEREOSELECTIVE RING-OPENING OF CHIRAL OXAZOLIDINES BY REFORMATSKY REAGENTS - AN ENANTIOSELECTIVE ENTRY TO BETA-AMINO ESTERS
ANDRES, C
GONZALEZ, A
PEDROSA, R
PEREZENCABO, A
[J]. TETRAHEDRON LETTERS, 1992, 33 (20) : 2895 - 2898
[2] REACTIONS OF RELEVANCE TO CHEMISTRY OF AMINOGLYCOSIDE ANTIBIOTICS .7. CONVERSION OF THIOCARBONATES INTO DEOXY-SUGARS
BARTON, DHR
SUBRAMANIAN, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (15): : 1718 - 1723
[3] ASYMMETRIC SYNTHESES OF OPTICALLY-ACTIVE ALPHA,BETA-DISUBSTITUTED BETA-AMINO ACIDS
BURGESS, K
LIU, LT
PAL, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) : 4758 - 4763
[4] REGIOSELECTIVE RING-OPENING OF CHIRAL EPOXYALCOHOLS BY PRIMARY AMINES
CANAS, M
POCH, M
VERDAGUER, X
MOYANO, A
PERICAS, MA
RIERA, A
[J]. TETRAHEDRON LETTERS, 1991, 32 (47) : 6931 - 6934
[5] STEREOSPECIFIC SYNTHESIS OF (2R,5R)-HEPT-6-YNE-2,5-DIAMINE - A POTENT AND SELECTIVE ENZYME-ACTIVATED IRREVERSIBLE INHIBITOR OF ORNITHINE DECARBOXYLASE (ODC)
CASARA, P
DANZIN, C
METCALF, B
JUNG, M
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11): : 2201 - 2207
[6] CASTEJON P, IN PRESS SYNTHETIC C
[7] ENANTIOMERICALLY PURE DIHYDROPYRIMIDINONES AS REAGENTS AND AUXILIARIES FOR ASYMMETRIC-SYNTHESIS
CHU, KS
NEGRETE, GR
KONOPELSKI, JP
LAKNER, FJ
WOO, NT
OLMSTEAD, MM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) : 1800 - 1812
[8] COREY EJ, 1979, TETRAHEDRON LETT, P399
[9] A NEW, STEREOSPECIFIC OLEFIN SYNTHESIS FROM 1,2-DIOLS
COREY, EJ
WINTER, RAE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (17) : 2677 - &
[10] A MILD PROCEDURE FOR THE CONVERSION OF 1,2-DIOLS TO OLEFINS
COREY, EJ
HOPKINS, PB
[J]. TETRAHEDRON LETTERS, 1982, 23 (19) : 1979 - 1982

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