A new general β-lactone synthesis

Barnett, William E.; McKenna, James C.

doi:10.1016/s0040-4039(01)96928-x

Cited by 22 publications

(2 citation statements)

References 6 publications

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“…[43] After deciding to attempt a later deprotection, TBS-protected carboxylic acid (17) was submitted for bromolactonization but frustratingly yielded intractable mixtures of non-polar products under standard bromolactonization conditions. [44] After consideration of these difficulties, it was decided to pursue a more readily removable ester. The trichloroethyl (Tce) ester group seemed an ideal candidate as its removal is performed by zinc reduction under mildly acidic conditions.…”

Section: Resultsmentioning

confidence: 99%

“…Pleasingly, hydrolysis of this ester occurred using zinc and acetic acid to afford the desired hydroxy acid (4) in 74% yield. [45] Bromolactonization was initially conducted using the method of Barnett [44] giving an unexpected result. A solution of the acid (4), in a biphasic mixture of dichloromethane and 10% aqueous sodium hydrogen carbonate, was treated with bromine in carbon tetrachloride.…”

Section: Resultsmentioning

confidence: 99%

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The Total Synthesis of ( - )-Tetrahydrolipstatin

Bodkin¹,

Humphries²,

McLeod³

2003

Aust. J. Chem.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

The Total Synthesis of ( - )-Tetrahydrolipstatin

Bodkin¹,

Humphries²,

McLeod³

2003

Aust. J. Chem.

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The synthesis of lactones and lactams

and

Wolfe

1993

PATAI'S Chemistry of Functional Groups

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Experimental and Computation Studies on Candida antarctica Lipase B‐Catalyzed Enantioselective Alcoholysis of 4‐Bromomethyl‐β‐lactone Leading to Enantiopure 4‐Bromo‐3‐hydroxybutanoate

Lim¹,

Park²,

Min³

et al. 2013

Adv Synth Catal

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Both enantiomers of optically pure 4‐bromo‐3‐hydroxybutanoate, which is an important chiral building block in the syntheses of various biologically active compounds including statins, were synthesized from rac‐4‐bromomethyl‐β‐lactone through kinetic resolution. Candida antarctica lipase B (CAL‐B) enantioselectively catalyzes the ring opening of the β‐lactone with ethanol to yield ethyl (R)‐4‐bromo‐3‐hydroxybutanoate with high enantioselectivity (E>200). The unreacted (S)‐4‐bromomethyl‐β‐lactone was converted to ethyl (S)‐4‐bromo‐3‐hydroxybutanoate (>99% ee), which can be further transformed to ethyl (R)‐4‐cyano‐3‐hydroxybutanoate, through an acid‐catalyzed ring opening in ethanol. Molecular modeling revealed that the stereocenter of the fast‐reacting enantiomer, (R)‐bromomethyl‐β‐lactone, is ∼2 Å from the reacting carbonyl carbon. In addition, the slow‐reacting enantiomer, (S)‐4‐bromomethyl‐β‐lactone, encounters steric hindrance between the bromo substituent and the side chain of the Leu278 residue, while the fast‐reacting enantiomer does not have any steric clash.

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A new general β-lactone synthesis

Cited by 22 publications

References 6 publications

The Total Synthesis of ( - )-Tetrahydrolipstatin

The Total Synthesis of ( - )-Tetrahydrolipstatin

The synthesis of lactones and lactams

Experimental and Computation Studies on Candida antarctica Lipase B‐Catalyzed Enantioselective Alcoholysis of 4‐Bromomethyl‐β‐lactone Leading to Enantiopure 4‐Bromo‐3‐hydroxybutanoate

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