Asymmetric synthesis of pre-protected α,α-disubstituted amino acids from tert-butanesulfinyl ketimines

被引：73

作者：

Borg, G ^{[1
]}

Chino, M ^{[1
]}

Ellman, JA ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 08期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(00)02300-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the asymmetric synthesis of pre-protected alpha,alpha -disubstituted amino acids is described. 5-Methylfuryllithium is added into sulfinyl ketimines 1 in the presence of AlMe3 to afford the sulfinamides 2 in 75-97% yields and with diastereoselectivities ranging from 75:25 to 99:1. Subsequent oxidation with RuCl3/NaIO4 affords tert-butanesulfonyl (Bus)-protected alpha,alpha -disubstituted amino acids 3 in 62-69% yields. Bus-protected amino acids readily undergo amide bond formation, after which the Bus group can be removed with TfOH/CH2Cl2 to afford the free amine. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1433 / 1436

页数：4

共 11 条

[1] Alvaro G, 1998, SYNTHESIS-STUTTGART, P1773
[2] Balaram P., 1992, CURR OPIN STRUC BIOL, V2, P845, DOI [DOI 10.1016/0959-440X(92)90110-S, 10.1016/0959-440X(92)90110-S]
[3] Stereoselective synthesis of quaternary α-amino acids.: Part 1:: Acyclic compounds
Cativiela, C
Diaz-de-Villegas, MD
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (20) : 3517 - 3599
[4] Asymmetric synthesis of α,α-dibranched amines by the trimethylaluminum-mediated 1,2-addition of organolithiums to tert-butanesulfinyl ketimines
Cogan, DA
Ellman, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) : 268 - 269
[5] tert-butylsulfonamide.: A new nitrogen source for catalytic aminohydroxylation and aziridination of olefins
Gontcharov, AV
Liu, H
Sharpless, KB
[J]. ORGANIC LETTERS, 1999, 1 (05) : 783 - 786
[6] Synthesis of enantiomerically pure N-tert-butanesulfinyl imines (tert-butanesulfinimines) by the direct condensation of tert-butanesulfinamide with aldehydes and ketones
Liu, GC
Cogan, DA
Owens, TD
Tang, TP
Ellman, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) : 1278 - 1284
[7] tert-butylsulfonyl (Bus), a new protecting group for amines
Sun, P
Weinreb, SM
Shang, MY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) : 8604 - 8608
[8] ALKYLATION AND PROTONATION OF CHIRAL SCHIFF-BASES - DIASTEREOSELECTIVITY AS A FUNCTION OF THE NATURE OF REACTANTS
TABCHEH, M
ELACHQAR, A
PAPPALARDO, L
ROUMESTANT, ML
VIALLEFONT, P
[J]. TETRAHEDRON, 1991, 47 (26) : 4611 - 4618
[9] THE DESIGN OF METABOLICALLY-STABLE PEPTIDE ANALOGS
VEBER, DF
FREIDINGER, RM
[J]. TRENDS IN NEUROSCIENCES, 1985, 8 (09) : 392 - 396
[10] Heteroarene-2-sulfonyl chlorides (BtsCl; ThsCl): Reagents for nitrogen protection and >99% racemization-free phenylglycine activation with SOCl2
Vedejs, E
Lin, SZ
Klapars, A
Wang, JB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (40) : 9796 - 9797

← 1 2 →