2-Azidoalcohols

The azidoalcohols (20) and (21) have been reacted with acid chlorides and alkyl chloride to give esters containing both azido and fluorodinitromethyl functionality. ... 

The spirocyclic phosphazenes (138) resulting from the reaction with 2-azidoalcohols dimerize <82TL853>. In the adducts of phenols with a heterodiene function in the 2-position <77ZN(B)84l> the phosphorus atom also becomes the center of a tricyclic system (139) (Scheme 45). 

Azidoalcohols (79, 81) can be accessed directly through the cerium-catalyzed addition of sodium azide onto mono-substituted epoxides. When the substituent is a simple alkyl or aryl group, nucleophilic attack at the more substituted epoxide carbon was observed i.e., 78 -> 79). However, when a phenoxy group was incorporated into the side chain (e.g., 80), a crossover to attack on the unsubstituted methylene carbon was encountered <99SC561>. 

P-Aminoalcohols may be generated from (3-azidoalcohols, which are commonly made from the opening of epoxides with azide ion as shown in Scheme 13 (91TL2533). After conversion of the alcohol... 

The cyclization of 7-aminoalcohols or 7-azidoalcohols can produce azetidines via activation with phosphines (81JOC3562,84JCS(P1)2415,85TL2809,92OPP209), as exemplified for the conversion (25) — (26) (83CC682, 84JCS(P1)2415>. 

Epoxides undergo bimolecular nucleophilic displacement reactions with azide ion to produce azidoalcohols (Table 2). Azide ion preferentially attacks saturated unsymmetrical epoxides at the less substituted carbon atom in accordance with the normal pattern of polar... 

Epoxides which are fused to alicyclic systems undergo ring opening with azide ion in the usual tram diaxial manner This is demonstrated by the formation of the /ran5-2-azidoalcohols (66) and (67) from cyclohexene oxide and cyclopentene oxide respectively . 

A considerable number of vicinal azidoalcohols have been synthesized by Ponsold and co-workers by reactions of epoxy-... 

Epoxides may be converted to aziridines with retention of configuration using a three-step procedure involving sulfur chemistry, as shown in Scheme 74 <92CC284>. Compare this stereochemical outcome with that observed above in the conversion of epoxides to aziridines via the / -azidoalcohol and triphenylphosphine, where both epoxide carbons undergo inversion of configuration. 

Utilization of 242 for preparation of Neu5Ac [141] required an introduction of the acetamido function. With this aim 242 was suitably blocked to give 246. Selective 5-OH-cxo tosylation and subsequent treatment with NaOMe in MeOH allowed to form a-epoxide 247. Opening of the oxirane ring by use of NaN3 afforded the azidoalcohol 248 as a sole product, easily transformed into methyl glycoside 249 as it is... 

In another approach, commercially available ethyl fran.y-cinnamate was used as starting material, and similar chemistry to that described above was performed, except that the cyclic sulfite 7.2.16 was opened directly with azide instead of being oxidized to sulfate the resulting azidoalcohol 7.2.17 had the opposite stereochemistry at C-2. The stereochemistry at C-2 was inverted by the Mitsonobu procedure to give... 

Sodium azide sulfuric acid 2-Azidoalcohols from oxido compds. 

Sodium azide/sulfuric acid 2-Azidoalcohols from oxido compounds s. 15, 370... 

The azide ion can also be used for stereoselective ring opening of epoxides. Reduction of the resulting S-azidoalcohol gives a S-aminoalcohol, as illustrated by the conversion of cyclohexene to frans-2-aminocyclohexanol. 

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