Allylation reactions of acylsilanes as synthetic equivalents of aldehydes, application to a stereocontrolled synthesis of (1S,2S,5S)-(10S)-and-(10R)-allyl myrtanol

被引：31

作者：

Bonini, BF ^{[1
]}

Comes-Franchini, M ^{[1
]}

Fochi, M ^{[1
]}

Mazzanti, G ^{[1
]}

Nanni, C ^{[1
]}

Ricci, A ^{[1
]}

机构：

[1] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 37期

关键词：

acylsilanes; allylation; homoallylic alcohols; myrtanol;

D O I：

10.1016/S0040-4039(98)01413-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The allylation of acylsilanes with tetraallyltin in the presence of catalytic amounts of Sc(OTf)(3) proceeded smoothly to afford the silylated homoallylic alcohols in good yields. Subsequent protiodesilylation gave the formal adducts of the corresponding aldehydes. The homochiral acylsilane 1l gave a reversal of asymmetric induction in the Sc(OTf)(3) catalyzed allylation and in the Sakurai reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6737 / 6740

页数：4

共 21 条

[1] Highly stereoselective route toward the synthesis of beta- and gamma-amino alcohols from homochiral alpha- and beta-amino acylsilanes as synthetic equivalents of alpha- and beta-amino aldehydes [J].

Bonini, BF ;

ComesFranchini, M ;

Mazzanti, G ;

Ricci, A ;

Sala, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (21) :7242-7243

[2] Chemistry of thioacylsilanes .11. Cyclic and open chain alpha-silyl vinyl sulfides as precursors of thioannulated cyclopentenones and thiofunctionalized enones [J].

Bonini, BF ;

Franchini, MC ;

Fochi, M ;

Mazzanti, G ;

Ricci, A .

TETRAHEDRON, 1997, 53 (23) :7897-7910

[3] CHEMISTRY OF SILYL THIOKETONES .7. SYNTHESIS, CYCLOADDITION AND OXIDATION OF CYCLOALKYL SILYL THIOKETONES AND DESILYLATION OF THE REACTION-PRODUCTS [J].

BONINI, BF ;

BUSI, F ;

DELAET, RC ;

MAZZANTI, G ;

THURING, JWJF ;

ZANI, P ;

ZWANENBURG, B .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (09) :1011-1018

[4] ASYMMETRIC ALLYLBORATION OF ACYLSILANES [J].

BUYNAK, JD ;

GENG, BL ;

UANG, SN ;

STRICKLAND, JB .

TETRAHEDRON LETTERS, 1994, 35 (07) :985-988

[5] SYNTHESIS OF ALPHA-SILYL KETONES VIA 1,3-DITHIANES [J].

COREY, EJ ;

SEEBACH, D ;

FREEDMAN, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (02) :434-&

[6] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].

DALE, JA ;

MOSHER, HS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519

[7] SUPER-ACID CATALYZED ADDITION OF ALLYLSILANES TO CARBONYL-COMPOUNDS - SYNTHETIC AND MECHANISTIC ASPECTS [J].

DAVIS, AP ;

JASPARS, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (16) :2111-2118

[8] SELECTIVE ALLYLATION OF CARBONYL-COMPOUNDS IN AQUEOUS-MEDIA [J].

EINHORN, C ;

LUCHE, JL .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 322 (02) :177-183

[9]

FLEMING I, 1991, J CHEM SOC P1, P2527

[10] DIASTEREOGENIC ADDITION OF CROTYLMETAL COMPOUNDS TO ALDEHYDES [J].

HOFFMANN, RW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1982, 21 (08) :555-566

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