Carboxyl Protecting Groups Stability

Methyl ester
	H2O:	pH < 1, 100°C	pH = 1, RT	pH = 4, RT	pH = 9, RT	pH = 12, RT	pH > 12, 100°C
	Bases:	LDA	NEt3, Py	t-BuOK	Others:	DCC	SOCl2
	Nucleophiles:	RLi	RMgX	RCuLi	Enolates	NH3, RNH2	NaOCH3
	Electrophiles:	RCOCl	RCHO	CH3I	Others:	:CCl2	Bu3SnH
	Reduction:	H2 / Ni	H2 / Rh	Zn / HCl	Na / NH3	LiAlH4	NaBH4
	Oxidation:	KMnO4	OsO4	CrO3 / Py	RCOOOH	I2, Br2, Cl2	MnO2 / CH2Cl2

T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 372-381, 383-387, 728-731.

t-Butyl ester
	H2O:	pH < 1, 100°C	pH = 1, RT	pH = 4, RT	pH = 9, RT	pH = 12, RT	pH > 12, 100°C
	Bases:	LDA	NEt3, Py	t-BuOK	Others:	DCC	SOCl2
	Nucleophiles:	RLi	RMgX	RCuLi	Enolates	NH3, RNH2	NaOCH3
	Electrophiles:	RCOCl	RCHO	CH3I	Others:	:CCl2	Bu3SnH
	Reduction:	H2 / Ni	H2 / Rh	Zn / HCl	Na / NH3	LiAlH4	NaBH4
	Oxidation:	KMnO4	OsO4	CrO3 / Py	RCOOOH	I2, Br2, Cl2	MnO2 / CH2Cl2

T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 372-381, 404-408, 728-731.

Benzyl ester
	H2O:	pH < 1, 100°C	pH = 1, RT	pH = 4, RT	pH = 9, RT	pH = 12, RT	pH > 12, 100°C
	Bases:	LDA	NEt3, Py	t-BuOK	Others:	DCC	SOCl2
	Nucleophiles:	RLi	RMgX	RCuLi	Enolates	NH3, RNH2	NaOCH3
	Electrophiles:	RCOCl	RCHO	CH3I	Others:	:CCl2	Bu3SnH
	Reduction:	H2 / Ni	H2 / Rh	Zn / HCl	Na / NH3	LiAlH4	NaBH4
	Oxidation:	KMnO4	OsO4	CrO3 / Py	RCOOOH	I2, Br2, Cl2	MnO2 / CH2Cl2

T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 372-381, 415-419, 728-731.

S-t-Butyl ester
	H2O:	pH < 1, 100°C	pH = 1, RT	pH = 4, RT	pH = 9, RT	pH = 12, RT	pH > 12, 100°C
	Bases:	LDA	NEt3, Py	t-BuOK	Others:	DCC	SOCl2
	Nucleophiles:	RLi	RMgX	RCuLi	Enolates	NH3, RNH2	NaOCH3
	Electrophiles:	RCOCl	RCHO	CH3I	Others:	:CCl2	Bu3SnH
	Reduction:	H2 / Ni	H2 / Rh	Zn / HCl	Na / NH3	LiAlH4	NaBH4
	Oxidation:	KMnO4	OsO4	CrO3 / Py	RCOOOH	I2, Br2, Cl2	MnO2 / CH2Cl2

T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 431-433, 728-731.

2-Alkyl-1,3-oxazoline
	H2O:	pH < 1, 100°C	pH = 1, RT	pH = 4, RT	pH = 9, RT	pH = 12, RT	pH > 12, 100°C
	Bases:	LDA	NEt3, Py	t-BuOK	Others:	DCC	SOCl2
	Nucleophiles:	RLi	RMgX	RCuLi	Enolates	NH3, RNH2	NaOCH3
	Electrophiles:	RCOCl	RCHO	CH3I	Others:	:CCl2	Bu3SnH
	Reduction:	H2 / Ni	H2 / Rh	Zn / HCl	Na / NH3	LiAlH4	NaBH4
	Oxidation:	KMnO4	OsO4	CrO3 / Py	RCOOOH	I2, Br2, Cl2	MnO2 / CH2Cl2

T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 1999, 433-435, 728-731.