Practical synthesis of bis-homoallylic alcohols from dialdehydes or their acetals

被引：17

作者：

Samoshin, VV ^{[1
]}

Gremyachinskiy, DE ^{[1
]}

Smith, LL ^{[1
]}

Bliznets, IV ^{[1
]}

Gross, PH ^{[1
]}

机构：

[1] Univ Pacific, Dept Chem, Stockton, CA 95211 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(02)01398-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bis-homoallylic alcohols were prepared in good yields by allylation of dialdehydes or their acetals with allyl bromide, tin(II) chloride and potassium iodide in water or water/THF. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：6329 / 6330

页数：2

共 31 条

[1] Intercalation of multiple carbon atoms between the carbonyls of α-diketones
Balskus, EP
Méndez-Andino, J
Arbit, RM
Paquette, LA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (20) : 6695 - 6704
[2] Bis ring closing olefin metathesis for the synthesis of unsaturated polycyclic ethers. O-membered ring cyclization in favor of C-membered ring cyclization
Baylon, C
Heck, MP
Mioskowski, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (09) : 3354 - 3360
[3] Organometallic reactions in aqueous media. The nature of the organotin intermediate in the tin-mediated allylation of carbonyl compounds
Chan, TH
Yang, Y
Li, CJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) : 4452 - 4455
[4] Chiral synthesis via organoboranes.: 46.: An efficient preparation of chiral pyridino- and thiopheno-18-crown-6 ligands from enantiomerically pure C2-symmetric pyridine- and thiophenediols
Chen, GM
Brown, HC
Ramachandran, PV
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) : 721 - 725
[5] Efficient syntheses of enantiomerically pure 1,2-dicyclohexenyl- and 1,2-dicyclohexyl-1,2-ethanediol using B-2-cyclohexen-1-yl-diisopinocampheylborane
Chen, GM
Ramachandran, PV
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (23) : 3935 - 3938
[6] SELECTIVE ALLYLATION OF CARBONYL-COMPOUNDS IN AQUEOUS-MEDIA
EINHORN, C
LUCHE, JL
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 322 (02) : 177 - 183
[7] HYDRATED SIGMA-BONDED ORGANOMETALLIC CATIONS IN ORGANIC-SYNTHESIS .1. ALLYL-STANNATION, CROTYL-STANNATION, 1-METHYLALLYL-STANNATION, CYCLOHEX-2-ENYL-STANNATION, AND CINNAMYL-STANNATION OF CARBONYL-COMPOUNDS IN WATER
FURLANI, D
MARTON, D
TAGLIAVINI, G
ZORDAN, M
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 341 (1-3) : 345 - 356
[8] Gewald R, 1996, SYNTHESIS-STUTTGART, P111
[9] CLEAVAGE AND OLIGOMERIZATION OF MALONDIALDEHYDE
GOMEZSANCHEZ, A
HERMOSIN, I
LASSALETTA, JM
MAYA, I
[J]. TETRAHEDRON, 1993, 49 (06) : 1237 - 1250
[10] AQUEOUS REACTIONS WITH A LEWIS-ACID AND AN ORGANOMETALLIC REAGENT - THE SCANDIUM TRIFLUOROMETHANESULFONATE-CATALYZED ALLYLATION REACTION OF CARBONYL-COMPOUNDS WITH TETRAALLYLTIN
HACHIYA, I
KOBAYASHI, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) : 6958 - 6960

← 1 2 3 4 →