UNIT 5 - Enolates-05-advanced aldol practice

UNIT 5 - Enolates-05-advanced aldol practice - SC6POC...

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SC6POC – O’Malley Enolates 5 Name: _______________ (Advanced aldol practice) © S. O’Malley 2010 NH O O Bn (S) - oxazolidinone i. n -BuLi ii. i. Cy 2 BOTf Et 3 N ii. N O O O Bn R' OH R ( OH back, anti ) Cl O R H R' O NH O O Bn ( R ) - oxazolidinone i. n -BuLi ii. i. Cy 2 BOTf Et 3 N ii. N O O O Bn R' OH R ( OH front, anti ) Cl O R H R' O NH O O Bn (S) - oxazolidinone i. n -BuLi ii. i. Bu 2 BOTf Et 3 N ii. N O O O Bn R' OH R ( OH back, syn ) Cl O R H R' O NH O O Bn ( R ) - oxazolidinone i. n -BuLi ii. i. Bu 2 BOTf Et 3 N ii. N O O O Bn R' OH R ( OH front, syn ) Cl O R H R' O 1. What are the products of the following: a. NH O O Bn i. n -BuLi ii. i. Bu 2 BOTf Et 3 N ii. Cl O H O Me NaOMe b. NH O O Bn i. n -BuLi ii. i. Cy 2 BOTf Et 3 N ii. Cl O Me LiBH 4 CHO c. NH O O Bn i. n -BuLi ii. i. Cy 2 BOTf Et 3 N ii. Cl O H Ph O i. MeNHOMe AlMe 3 ii. Me 2 CuLi
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2. CHALLENGE: The following aldol reaction occurs with very high stereoselectivity. The starting ketone selectively forms the Z
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UNIT 5 - Enolates-05-advanced aldol practice - SC6POC...

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