+ Site Statistics
References:
54,258,434
Abstracts:
29,560,870
PMIDs:
28,072,757
+ Search Articles
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ PDF Full Text
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Translate
+ Recently Requested

In- or in(I)-employed diastereoselective Reformatsky-type reactions with ketones: 1H NMR investigations on the active species



In- or in(I)-employed diastereoselective Reformatsky-type reactions with ketones: 1H NMR investigations on the active species



Organic Letters 6(24): 4475-4478



An efficient In- or In(I)-based stereoselective C-C bond formation is reported; the diastereoselective Reformatsky-type reactions of ketones. The predominant formations of anti isomers, confirmed by the X-ray structure analyses of ester derivatives of respective alcohols 9a(1)() and 13a(1)(), conclusively revealed the stereochemistry of the reaction path. (1)H NMR investigations revealed the formation of two types of alpha-metalated transient species from alpha-halo esters with In or In(I) halides. [reaction: see text]

(PDF emailed within 0-6 h: $19.90)

Accession: 049318611

Download citation: RISBibTeXText

PMID: 15548054

DOI: 10.1021/ol0482846


Related references

In- or In(I)-employed tailoring of the stereogenic centers in the Reformatsky-type reactions of simple ketones, alpha-alkoxy ketones, and beta-keto esters. Journal of Organic Chemistry 70(25): 10408-10419, 2005

Reformatsky-type aldol reactions of 4-bromo-4,4-difluoroacetoacetate with aldehydes and ketones. Tetrahedron Letters 42(33): 5741-5744, 13 August, 2001

Synthesis of carbohydrate derived alpha methylene gamma lactones by diastereoselective low temperature reformatsky type reactions. Journal of Carbohydrate Chemistry 5(3): 459-468, 1986

Diastereoselective synthesis of pentasubstituted gamma-butyrolactones from silyl glyoxylates and ketones through a double Reformatsky reaction. Angewandte Chemie 48(20): 3689-3691, 2009

Recent advances in the diastereoselective Reformatsky-type reaction. Chemical Society Reviews 42(3): 937-949, 2013

Highly diastereoselective reformatsky-type reaction promoted by tin iodide ate complex. Organic Letters 4(2): 301-303, 2002

Ti-catalyzed reformatsky-type coupling between alpha-halo ketones and aldehydes. Journal of Organic Chemistry 73(4): 1616-1619, 2008

Reformatsky-type addition of esters of α-halogeno carboxylic acids to aldehydes and ketones in the presence of Fe(CO)5. Russian Chemical Bulletin 48(6): 1121-1127, 1999

High chelation control of three contiguous stereogenic centers in the Reformatsky reactions of indium enolates with alpha-hydroxy ketones: unexpected stereochemistry of lactone formation. Organic Letters 8(14): 3029-3032, 2006

Convenient asymmetric synthesis of beta-trifluoromethyl-beta-amino acid, beta-amino ketones, and gamma-amino alcohols via Reformatsky and Mannich-type reactions from 2-trifluoromethyl-1,3-oxazolidines. Journal of Organic Chemistry 71(5): 2159-2162, 2006

Highly diastereoselective aldol reactions of chiral methyl ketones. Journal Of Organic Chemistry. 58(16): 4191-4193, 1993

Highly diastereoselective aldol reactions of alpha-amino methyl ketones. Abstracts of Papers American Chemical Society 206(1-2): ORGN 428, 1993

Reactions of an endoperoxide with chiral ketones diastereoselective formation of 1 2 4 trioxanes and 1 3 dioxolanes. Tetrahedron Letters 32(49): 7243-7246, 1991

Sequential Multicomponent Reactions and a Cu-Mediated Rearrangement: Diastereoselective Synthesis of Tricyclic Ketones. Organic Letters 17(23): 5866-5869, 2015

Me(2)Zn as a radical source in Reformatsky-type reactions. Chemical Communications: 469-470, 2009