A Facile Method for the Preparation of MOM-Protected Carbamates

被引：20

作者：

Barnes, David M. ^{[1
]}

Barkalow, Mang ^{[1
]}

Plata, Daniel J. ^{[1
]}

机构：

[1] Abbott Labs, GPRD Proc Res & Dev, Abbott Pk, IL 60064 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 02期

关键词：

AMINO-ACID DERIVATIVES; ALKYLATION; CHIRALITY; ENOLATE;

D O I：

10.1021/ol8022769

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method for the preparation of MOM-protected carbamates is described that avoids the use of MOM-Cl, a regulated carcinogen. The two-step, one-pot procedure generates a reactive N-chloromethyl carbamate that is quenched with methanol to afford MOM-protected carbamates. The process is tolerant of a variety of functionalities, including Boc, sulfonamide, and acetamide protecting groups. Mild conditions for the removal of the MOM group are also described; selective deprotection of the MOM group in the presence of a Boc group has been demonstrated.

引用

页码：273 / 275

页数：3

共 21 条

[1] Total synthesis of avrainvillamide (CJ-17,665) and stephacidin B [J].

Baran, PS ;

Guerrero, CA ;

Hafensteiner, BD ;

Ambhaikar, NB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (25) :3892-3895

[2] SYNTHESIS OF THE TRICYCLIC HEART OF MANZAMINES [J].

BRANDS, KMJ ;

PANDIT, UK .

TETRAHEDRON LETTERS, 1989, 30 (11) :1423-1426

[3] DARSTELLUNG VON ALPHA-OXY-SULFONEN UND ALPHA-AMINO-SULFONEN SOWIE VON SULFINSAUREN SALZEN ORGANISCHER BASEN .1. UBER POLYMERISATIONEN UND POLYMERISATIONSKATALYSATOREN [J].

BREDERECK, H ;

BADER, E .

CHEMISCHE BERICHTE-RECUEIL, 1954, 87 (01) :129-139

[4]

ESCH PM, 1988, TETRAHEDRON LETT, V29, P367

[5]

GREEN TW, 1999, PROTECTIVE GROUPS OR

[6]

KAWABATA, 2005, SYNTHESIS-STUTTGART, P505

[7] Stereochemical study on α-alkylation of β-branched α-amino acid derivatives via memory of chirality [J].

Kawabata, T ;

Chen, JY ;

Suzuki, H ;

Fuji, K .

SYNTHESIS-STUTTGART, 2005, (08) :1368-1377

[8] Control of the enantioselectivity of alkylation of phenylalanine derivatives by regulation of the aggregate structure of chiral enolate intermediates [J].

Kawabata, T ;

Kawakami, SP ;

Shimada, S ;

Fuji, K .

TETRAHEDRON, 2003, 59 (07) :965-974

[9]

Kawabata T, 2000, ANGEW CHEM INT EDIT, V39, P2155, DOI 10.1002/1521-3773(20000616)39:12<2155::AID-ANIE2155>3.0.CO

[10]

2-N

← 1 2 3 →