R-BINAL

Lithium aluminum hydride-2,2 -dihydroxy-l,l -binaphthyl ((R)-BINAL) [18531-94-7] -Lithium aluminum hydride-2,2 -dihydroxy-l,l -binaphthyl ((S)-BINAL) Preparation ... 

R) -BINAL-H (R)-2,2 -Dihydroxy-1,1 -binaphthol-lithium aluminum hydride,... 

The hydride donor of the Noyori reduction of ketones is the hydrido aluminate. R-BINAL-H shown in Figure 8.18 or its enantiomer. S -BINAL-H.The new C H bond is presumably formed via a cyclic six-membered transition state of stereostructure A. Unfortunately, there is no easy way to rationalize why enantioselectivity in this kind of addition is limited to substrates in which the carbonyl group is flanked by one conjugated substituent (O C, aryl, C—C). 

OXAZOLIDINECARBOXYLATE has previously been described in Volume 70 of Organic Sytheses. An alternative procedure for the preparation of this compound is presented in this volume along with its use in a dia-stereoselective addition reaction with 2-TRIMETHYLSILYLTH1AZOLE to provide a compound bearing a 2-amino-1,3-diol substructure that appears in a variety of natural products. The conversion of abundantly available isosorbide into OSO ISOPROPYLIDENE-l ti-DIANHYDRO-d-GLUCITOL provides a potentially useful carbohydrate-deri ved material for the use in complex tetrahydrofuran synthesis. Finally, asymmetric reduction of an a,j9-unsaturated acylstannane with (R)-BINAL provides access to (S,E)-l-(METHOXYMETHOXY)-l-TRIBUTYLSTANNYL-2-BUTENE, an a-alkoxy allylstannane that has been used in enantioselective vicinal diol synthesis amongst other transformations. 

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