Rapid syntheses of benzopyrans from o-OBOC salicylaldehydes and salicyl alcohols:: A three-component reaction

被引：67

作者：

Jones, RM ^{[1
]}

Selenski, C ^{[1
]}

Pettus, TRR ^{[1
]}

机构：

[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 20期

关键词：

D O I：

10.1021/jo020224v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder reactions of o-quinone methides generated from OBOC-salicylic aldehydes and alcohols are described, allowing for the synthesis of various substituted benzopyrans. The low temperatures employed for this procedure enable high diastereoselectivity in reactions with beta-substituted o-quinone methides.

引用

页码：6911 / 6915

页数：5

共 19 条

[1] REACTIONS OF 2-PHENYL-4H-1,3,2-BENZODIOXABORIN, A STABLE ORTHO-QUINONE METHIDE PRECURSOR [J].

CHAMBERS, JD ;

CRAWFORD, J ;

WILLIAMS, HWR ;

DUFRESNE, C ;

SCHEIGETZ, J ;

BERNSTEIN, MA ;

LAU, CK .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (06) :1717-1732

[2] Effect of a novel antibiotic, heliquinomycin, on DNA helicase and cell growth [J].

Chino, M ;

Nishikawa, K ;

Yamada, A ;

Ohsono, M ;

Sawa, T ;

Hanaoka, F ;

Ishizuka, M ;

Takeuchi, T .

JOURNAL OF ANTIBIOTICS, 1998, 51 (05) :480-486

[3] SYNTHESIS OF CYCLIC AND ACYCLIC ENOL ETHERS (VINYL ETHERS) [J].

GASSMAN, PG ;

BURNS, SJ ;

PFISTER, KB .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1449-1457

[4]

HOARAU C, 2002, IN PRESS MOLECULES

[5] A NEW SYNTHESIS OF ORTHO-QUINONEMETHIDES AND THEIR INTERMOLECULAR AND INTRAMOLECULAR CYCLIZATION REACTIONS [J].

INOUE, T ;

INOUE, S ;

SATO, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (04) :1062-1068

[6] A mild anionic method for generating o-quinone methides:: Facile preparations of ortho-functionalized phenols [J].

Jones, RM ;

Van de Water, RW ;

Lindsey, CC ;

Hoarau, C ;

Ung, T ;

Pettus, TRR .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (10) :3435-3441

[7] FUNCTIONALIZED ENAMINES .32. REACTION OF BETA-AMINO-ALPHA, BETA-UNSATURATED ESTERS AND AMIDES WITH BENZYL AND CINNAMYL BROMIDES [J].

KANNER, CB ;

PANDIT, UK .

TETRAHEDRON, 1982, 38 (24) :3597-3604

[8] 1-amino-3-siloxy-1,3-butadienes: Highly reactive dienes for the Diels-Alder reaction [J].

Kozmin, SA ;

Janey, JM ;

Rawal, VH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) :3039-3052

[9] Silyl cuprate couplings:: Less silicon, accelerated, yet catalytic in copper [J].

Lipshutz, BH ;

Sclafani, JA ;

Takanami, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (16) :4021-4022

[10] A NOVEL REDUCTION OF CARBONYL TO METHYLENE BY ACTION OF SODIUM BOROHYDRIDE [J].

MCLOUGHLIN, BJ .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (10) :540-+

← 1 2 →