ON THE REVERSAL OF THE STEREOSELECTIVITY IN THE EVANS ALDOL REACTION OF ALPHA-AMINO ALDEHYDES

被引：31

作者：

HAYASHI, K ^{[1
]}

HAMADA, Y ^{[1
]}

SHIOIRI, T ^{[1
]}

机构：

[1] NAGOYA CITY UNIV,FAC PHARMACEUT SCI,TANABE DORI,MIZUHO KU,NAGOYA,AICHI 467,JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 49期

关键词：

EVANS ALDOL REACTION; STEREOSELECTIVITY; ALPHA-AMINO ALDEHYDE; DOLASTATIN-10; SYN AND ANTI ISOMERS;

D O I：

10.1016/0040-4039(91)80500-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reversal of the stereoselectivity in the Evans aldol reaction of Boc-(S)-prolinal (3), observed during the total synthesis of dolastatin 10 (1), was proved to be due to the amounts of dibutylboron triflate and triethylamine. (R)-Alaninal derivatives (14) also showed the analogous reversal of the stereoselectivity.

引用

页码：7287 / 7290

页数：4

共 10 条

[1] ACYCLIC STEREOSELECTION .48. REVERSAL OF STEREOCHEMISTRY IN THE ALDOL REACTIONS OF A CHIRAL BORON ENOLATE
DANDA, H
HANSEN, MM
HEATHCOCK, CH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) : 173 - 181
[2] (2S,3S,4R)-4-AMINO-3-HYDROXY-2-METHYLPENTANOIC ACID - ENANTIOSELECTIVE SYNTHESIS OF AN AMINO-ACID CONSTITUENT OF BLEOMYCIN
DIPARDO, RM
BOCK, MG
[J]. TETRAHEDRON LETTERS, 1983, 24 (44) : 4805 - 4808
[3] GAGE JR, 1989, ORG SYNTH, V68, P83
[4] EFFICIENT STEREOSELECTIVE SYNTHESIS OF DOLASTATIN-10, AN ANTINEOPLASTIC PEPTIDE FROM A SEA HARE
HAMADA, Y
HAYASHI, K
SHIOIRI, T
[J]. TETRAHEDRON LETTERS, 1991, 32 (07) : 931 - 934
[5] NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .67. A GENERAL-SYNTHESIS OF DERIVATIVES OF OPTICALLY PURE 2-(1-AMINOALKYL)THIAZOLE-4-CARBOXYLIC ACIDS
HAMADA, Y
SHIBATA, M
SUGIURA, T
KATO, S
SHIOIRI, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (07) : 1252 - 1255
[6] HAMADA Y, 1982, CHEM PHARM BULL, V30, P1921
[7] Heathcock C., 1990, ALDRICHIM ACTA, V23, P99
[8] ANTINEOPLASTIC AGENTS .189. THE ABSOLUTE-CONFIGURATION AND SYNTHESIS OF NATURAL (-)-DOLASTATIN-10
PETTIT, GR
SINGH, SB
HOGAN, F
LLOYDWILLIAMS, P
HERALD, DL
BURKETT, DD
CLEWLOW, PJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) : 5463 - 5465
[9] ANTINEOPLASTIC AGENTS .136. THE ISOLATION AND STRUCTURE OF A REMARKABLE MARINE ANIMAL ANTINEOPLASTIC CONSTITUENT - DOLASTATIN 10
PETTIT, GR
KAMANO, Y
HERALD, CL
TUINMAN, AA
BOETTNER, FE
KIZU, H
SCHMIDT, JM
BACZYNSKYJ, L
TOMER, KB
BONTEMS, RJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (22) : 6883 - 6885
[10] AN EXPEDITIOUS SYNTHESIS OF DOLASTATIN-10
TOMIOKA, K
KANAI, M
KOGA, K
[J]. TETRAHEDRON LETTERS, 1991, 32 (21) : 2395 - 2398

← 1 →