Phosphine-catalyzed synthesis of 1,3-dioxan-4-ylidenes

被引：147

作者：

Zhu, XF ^{[1
]}

Henry, CE ^{[1
]}

Wang, J ^{[1
]}

Dudding, T ^{[1
]}

Kwon, O ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 07期

关键词：

D O I：

10.1021/ol050203y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A phosphine-catalyzed reaction of an allenoate with aldehydes furnished (2,6-diaryl-[1,3]dioxan-4-ylidene)-acetates 4 in excellent to moderate yields with complete diastereoselectivity and high E/Z-selectivities. Upon removal of the acetal functionality in this domino reaction product 4, delta-hydroxy-beta-ketoester 11 was obtained. The reported vinylphosphonium-based approach provides a new way to achieve a synthesis of 6-hydroxy-beta-ketoesters that differs from the classical dianion-based approach.

引用

页码：1387 / 1390

页数：4

共 32 条

[1] 5-ENDO-TRIGONAL REACTIONS - DISFAVORED RING-CLOSURE [J].

BALDWIN, JE ;

CUTTING, J ;

DUPONT, W ;

KRUSE, L ;

SILBERMAN, L ;

THOMAS, RC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :736-738

[2] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[3] The asymmetric Baylis-Hillman reaction [J].

Brzezinski, LJ ;

Rafel, S ;

Leahy, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (18) :4317-4318

[4]

Caine D., 1991, COMPREHENSIVE ORGANI, V3

[5] FACILE DIASTEREOSELECTIVE SYNTHESIS OF 2,6-DIALKYL-5-METHYLENE-1,3-DIOXAN-4-ONES VIA ALPHA-ACTIVATED VINYL ESTERS [J].

DREWES, SE ;

EMSLIE, ND ;

KARODIA, N ;

KHAN, AA .

CHEMISCHE BERICHTE, 1990, 123 (06) :1447-1448

[6] A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol [J].

Du, YS ;

Lu, XY .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6463-6465

[7] Highly regioselective construction of spirocycles via phosphine-catalyzed [3+2]-cycloaddition [J].

Du, YS ;

Lu, XY ;

Yu, YH .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8901-8905

[8] Amine-catalyzed coupling of allenic esters to α,β-unsaturated carbonyls [J].

Evans, CA ;

Miller, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12394-12395

[9] DIASTEREOSELECTIVE SYNTHESIS OF PROTECTED SYN 1,3-DIOLS BY BASE-CATALYZED INTRAMOLECULAR CONJUGATE ADDITION OF HEMIACETAL-DERIVED ALKOXIDE NUCLEOPHILES [J].

EVANS, DA ;

GAUCHETPRUNET, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2446-2453

[10] ALKYLATION OF DIANIONS OF BETA-KETO-ESTERS [J].

HUCKIN, SN ;

WEILER, L .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) :1082-1087

← 1 2 3 4 →