Hydrogen-bonding catalysis and inhibition by simple solvents in the stereoselective kinetic epoxide-opening spirocyclization of glycal epoxides to form spiroketals

Journal of the American Chemical Society

Volumn 133, Issue 20, 2011, Pages 7916-7925

  Wurst, Jacqueline M ^a   Liu, Guodong ^a   Tan, Derek S ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERIC CARBON; COSOLVENTS; DIFFERENTIAL REACTION; ELECTROPHILES; EXPERIMENTAL DATA; FIRST-ORDER; HAMMETT ANALYSIS; HYDROGEN BONDINGS; INVERSION OF CONFIGURATION; METHYL GLYCOSIDES; NATURAL PRODUCTS; SECOND ORDERS; SIDE REACTIONS; SIDE-CHAINS; SPIROCYCLIZATION; SPIROKETALS; STEREO-SELECTIVE; STRUCTURAL MOTIFS; TRANSITION STATE;

ACETONE; CATALYSIS; HYDROGEN; HYDROGEN BONDS; KINETICS; OXYGEN; SOLVENTS; STEREOSELECTIVITY; SUGARS;

REACTION RATES;

ACETAL; ACETONE; ELECTROPHILE; EPOXIDE; HYDROGEN; METHYLGLYCOSIDE; NATURAL PRODUCT; NUCLEOPHILE; OXYGEN; SOLVENT; SPIRO COMPOUND; SULFUR;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CONCENTRATION (PARAMETERS); CYCLIZATION; EPOXIDE OPENING SPIROCYCLIZATION; HYDROGEN BOND; INHIBITION KINETICS; REACTION ANALYSIS; RING OPENING; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE;

CATALYSIS; CYCLIZATION; EPOXY COMPOUNDS; HYDROGEN BONDING; KINETICS; SOLVENTS; STEREOISOMERISM;

EID: 79957767302     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja201249c     Document Type: Article

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